Skip to main content
SpringerLink
Log in

Acetylation of Alcohols Catalyzed by Dodeca-tungsto(molybdo)phosphoric acid

  • Published:
Monatshefte für Chemie / Chemical Monthly Aims and scope Submit manuscript

Summary.

Acetylation of primary, secondary, and tertiary alcohols was carried out in some refluxing alkyl acetates and in two carboxylic acids with the participation of catalytic amounts of H3PW12O40, H3PMo12O40, and H14P5W30O110 with good yields and high stereo(regio)specificity under mild reaction condition. H3PW12O40 and H3PMo12O40 have also shown excellent reactivity in the formylation of 1-butanol with ethyl formate at room temperature and in short reaction times. Heteropolyacid catalysts could be separated after a simple work up and reused for several times.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

References

  • TW Greene PGM Wuts (1999) Protective Groups in Organic Synthesis EditionNumber3 Wiley New York

    Google Scholar 

  • AK Chakraborti MK Nayak L Sharma (2002) J Org Chem 67 1776 Occurrence Handle1:CAS:528:DC%2BD38XhtFKnur8%3D Occurrence Handle10.1021/jo010611p

    Article  CAS  Google Scholar 

  • AK Chakraborti MK Nayak L Sharma (2002) J Org Chem 67 2541 Occurrence Handle1:CAS:528:DC%2BD38XhvFynsbs%3D Occurrence Handle10.1021/jo0163039

    Article  CAS  Google Scholar 

  • AK Chakraborti L Sharma U Sharma (2001) Tetrahedron 57 9343 Occurrence Handle1:CAS:528:DC%2BD3MXnvFWls7s%3D Occurrence Handle10.1016/S0040-4020(01)00922-X

    Article  CAS  Google Scholar 

  • AK Chakraborti MK Nayak L Sharma (1999) J Org Chem 64 8027 Occurrence Handle1:CAS:528:DyaK1MXlvFKiur4%3D Occurrence Handle10.1021/jo990780y

    Article  CAS  Google Scholar 

  • Frannklin AS (1999) J Chem Soc Perkin Trans 1 3537

  • EFV Scriven (1983) Chem Soc Rev 12 366 Occurrence Handle10.1039/cs9831200129

    Article  Google Scholar 

  • E Vedejs ST Diver (1993) J Am Chem Soc 115 3358 Occurrence Handle1:CAS:528:DyaK3sXkt1Oku70%3D Occurrence Handle10.1021/ja00061a056

    Article  CAS  Google Scholar 

  • K Ishihara M Kuboto H Kurihara H Yamamoto (1995) J Am Chem Soc 117 4413 Occurrence Handle1:CAS:528:DyaK2MXkvVajurs%3D Occurrence Handle10.1021/ja00120a030

    Article  CAS  Google Scholar 

  • PA Procopiou SPD Baugh SS Flask GGA Ingliss (1998) J Org Chem 63 2342 Occurrence Handle1:CAS:528:DyaK1cXhs12rtrk%3D Occurrence Handle10.1021/jo980011z

    Article  CAS  Google Scholar 

  • P Sarvanan VK Singh (1999) Tetrahedron Lett 40 2611 Occurrence Handle10.1016/S0040-4039(99)00229-4

    Article  Google Scholar 

  • S Chandrasekhar T Ramchander M Takhi (1998) Tetrahedron Lett 39 3263 Occurrence Handle1:CAS:528:DyaK1cXjt1Srsrk%3D Occurrence Handle10.1016/S0040-4039(98)00465-1

    Article  CAS  Google Scholar 

  • Chaun KK, Frost CG, Love I, Waite D (1999) Syn lett 1743

  • J Iqbal RR Srivastava (1992) J Org Chem 57 2001 Occurrence Handle1:CAS:528:DyaK38XhsFSrsbk%3D Occurrence Handle10.1021/jo00033a020

    Article  CAS  Google Scholar 

  • Kumar P, Pandey RK, Bodas MS, Dongare MK (2001) Syn lett 206

  • N Mizuno M Misono (1998) Chem Rev 98 199 Occurrence Handle1:CAS:528:DyaK1cXotVSgsA%3D%3D Occurrence Handle10.1021/cr960401q

    Article  CAS  Google Scholar 

  • CL Hill GM Prosser-McCartha (1995) Coordn Chem Rev 143 407 Occurrence Handle1:CAS:528:DyaK2MXptlSktrk%3D Occurrence Handle10.1016/0010-8545(95)01141-B

    Article  CAS  Google Scholar 

  • Y Zhang S Wu J Wang (1998) Ferzicuihua 2 279

    Google Scholar 

  • Okano T, Miyamoto K, Kiji J (1995) Chem Lett 245

  • Izumi Y, Urabe K, Onaka M (1992) In Zeolite, Clay and Heteropoly Acid in Organic Reactions, Kodansha/VCH, Tokyo

  • N Nojiri M Misono (1993) Appl Catal 95 559

    Google Scholar 

  • MH Alizadeh H Razavi FF Bamoharram (2003) J Mol Catal A Chemical 200 105 Occurrence Handle10.1016/S1381-1169(03)00043-8 Occurrence Handle1:CAS:528:DC%2BD3sXjs1ChtL8%3D

    Article  CAS  Google Scholar 

  • MH Alizadeh R Tayebee (2005) J Braz Chem Soc 16 108 Occurrence Handle1:CAS:528:DC%2BD2MXisVSrtbw%3D Occurrence Handle10.1590/S0103-50532005000100017

    Article  CAS  Google Scholar 

  • Alizadeh MH, Holman KT, Mirzaei M, Razavi H (2006) Polyhedron, in press

  • MH Alizadeh H Razavi FF Bamoharram MK Hassanzadeh R Khoshnavazi FM Zonoz (2003) Kinetics & Catalysis 44 524 Occurrence Handle1:CAS:528:DC%2BD3sXmt1ahu7w%3D Occurrence Handle10.1023/A:1025142101029

    Article  CAS  Google Scholar 

  • MH Alizadeh H Razavi FM Zonoz MR Mohammadi (2003) Polyhedron 22 933 Occurrence Handle1:CAS:528:DC%2BD3sXhvFSmsLY%3D Occurrence Handle10.1016/S0277-5387(03)00024-X

    Article  CAS  Google Scholar 

  • IV Kozhevnikov (1998) Chem Rev 98 171 Occurrence Handle1:CAS:528:DyaK1cXotVSgsw%3D%3D Occurrence Handle10.1021/cr960400y

    Article  CAS  Google Scholar 

  • IV Kozhevnikov (1995) Catal Rev Sci Eng 37 311 Occurrence Handle1:CAS:528:DyaK2MXmtVensr0%3D

    CAS  Google Scholar 

  • T Okuhara N Mizuno M Misono (1996) Adv Catal 41 113 Occurrence Handle1:CAS:528:DyaK28XltFyjtb4%3D Occurrence Handle10.1016/S0360-0564(08)60041-3

    Article  CAS  Google Scholar 

  • K Takahashi M Shibagaki H Matsushita (1989) Bull Chem Soc Jpn 62 2353 Occurrence Handle1:CAS:528:DyaK3cXhsFOgs74%3D Occurrence Handle10.1246/bcsj.62.2353

    Article  CAS  Google Scholar 

  • It should be noted that acetylation of tbutanol was reversible in this catalytic system

  • HJ Ringold B Loeken G Rosenkranz F Sondheimer (1956) J Am Chem Soc 78 816 Occurrence Handle1:CAS:528:DyaG28XmvFGjtw%3D%3D Occurrence Handle10.1021/ja01585a030

    Article  CAS  Google Scholar 

  • Fernandez I, Garcia B, Munoz S, Perdo JR, Salud R (1993) Syn lett 489

  • Neveux M, Bruneau C, Dixneuf PH (1991) J Chem Soc Perkin Trans 1 1197

  • EO North (1993) Inorg Synth 1 129

    Google Scholar 

  • H Wu (1920) J Biol Chem 43 189 Occurrence Handle1:CAS:528:DyaB3cXhsFGntg%3D%3D

    CAS  Google Scholar 

  • C Brevard R Schimpf G Tourne CM Tourne (1983) J Am Chem Soc 105 7059 Occurrence Handle1:CAS:528:DyaL2cXivVOlsw%3D%3D Occurrence Handle10.1021/ja00362a008

    Article  CAS  Google Scholar 

  • Bamoharram FF (2003) Ph.D. Thesis, Department of Chemistry, Ferdowsi University, Iran

  • MH Alizadeh SP Harmalker Y Jeanin MT Pope (1985) J Am Chem Soc 107 2662 Occurrence Handle1:CAS:528:DyaL2MXhslyjtLs%3D Occurrence Handle10.1021/ja00295a019

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Department of Chemistry, Sabzevar University, Sabzevar, Iran

    Reza Tayebee

  2. Department of Chemistry, Ferdowsi University, Mashhad, Iran

    Mohammad H. Alizadeh

Authors
  1. Reza Tayebee
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Mohammad H. Alizadeh
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Reza Tayebee.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Tayebee, R., Alizadeh, M. Acetylation of Alcohols Catalyzed by Dodeca-tungsto(molybdo)phosphoric acid. Monatsh. Chem. 137, 1063–1069 (2006). https://doi.org/10.1007/s00706-006-0507-z

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s00706-006-0507-z

Search

Navigation