A simple and versatile method for the synthesis of acetals from aldehydes and ketones using bismuth triflate

Nicholas M. Leonard; Matthew C. Oswald; Derek A. Freiberg; Bryce A. Nattier; Russell C. Smith; Ram S. Mohan

doi:10.1021/jo0258249

A simple and versatile method for the synthesis of acetals from aldehydes and ketones using bismuth triflate

Nicholas M. Leonard, Matthew C. Oswald, Derek A. Freiberg, Bryce A. Nattier, Russell C. Smith, Ram S. Mohan^*

^*Corresponding author for this work

Physical Medicine and Rehabilitation

Research output: Contribution to journal › Article › peer-review

162 Scopus citations

Abstract

Acetals are obtained in good yields by treatment of aldehydes and ketones with trialkyl orthoformate and the corresponding alcohol in the presence of 0.1 mol % Bi(OTf)₃·4H₂O. A simple procedure for the formation of acetals of diaryl ketones has also been developed. The conversion of carbonyl compounds to the corresponding 1,3-dioxolane using ethylene glycol is also catalyzed by Bi(OTf)₃· 4H₂O (1 mol %). Two methods, both of which avoid the use of benzene, have been developed.

Original language	English (US)
Pages (from-to)	5202-5207
Number of pages	6
Journal	Journal of Organic Chemistry
Volume	67
Issue number	15
DOIs	https://doi.org/10.1021/jo0258249
State	Published - Jul 26 2002

ASJC Scopus subject areas

Organic Chemistry

Access to Document

10.1021/jo0258249

Cite this

@article{b34480d7068e4940b8b5442f1cb06824,

title = "A simple and versatile method for the synthesis of acetals from aldehydes and ketones using bismuth triflate",

abstract = "Acetals are obtained in good yields by treatment of aldehydes and ketones with trialkyl orthoformate and the corresponding alcohol in the presence of 0.1 mol % Bi(OTf)3·4H2O. A simple procedure for the formation of acetals of diaryl ketones has also been developed. The conversion of carbonyl compounds to the corresponding 1,3-dioxolane using ethylene glycol is also catalyzed by Bi(OTf)3· 4H2O (1 mol %). Two methods, both of which avoid the use of benzene, have been developed.",

author = "Leonard, {Nicholas M.} and Oswald, {Matthew C.} and Freiberg, {Derek A.} and Nattier, {Bryce A.} and Smith, {Russell C.} and Mohan, {Ram S.}",

year = "2002",

month = jul,

day = "26",

doi = "10.1021/jo0258249",

language = "English (US)",

volume = "67",

pages = "5202--5207",

journal = "Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "American Chemical Society",

number = "15",

}

TY - JOUR

T1 - A simple and versatile method for the synthesis of acetals from aldehydes and ketones using bismuth triflate

AU - Leonard, Nicholas M.

AU - Oswald, Matthew C.

AU - Freiberg, Derek A.

AU - Nattier, Bryce A.

AU - Smith, Russell C.

AU - Mohan, Ram S.

PY - 2002/7/26

Y1 - 2002/7/26

N2 - Acetals are obtained in good yields by treatment of aldehydes and ketones with trialkyl orthoformate and the corresponding alcohol in the presence of 0.1 mol % Bi(OTf)3·4H2O. A simple procedure for the formation of acetals of diaryl ketones has also been developed. The conversion of carbonyl compounds to the corresponding 1,3-dioxolane using ethylene glycol is also catalyzed by Bi(OTf)3· 4H2O (1 mol %). Two methods, both of which avoid the use of benzene, have been developed.

AB - Acetals are obtained in good yields by treatment of aldehydes and ketones with trialkyl orthoformate and the corresponding alcohol in the presence of 0.1 mol % Bi(OTf)3·4H2O. A simple procedure for the formation of acetals of diaryl ketones has also been developed. The conversion of carbonyl compounds to the corresponding 1,3-dioxolane using ethylene glycol is also catalyzed by Bi(OTf)3· 4H2O (1 mol %). Two methods, both of which avoid the use of benzene, have been developed.

UR - http://www.scopus.com/inward/record.url?scp=0037178495&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0037178495&partnerID=8YFLogxK

U2 - 10.1021/jo0258249

DO - 10.1021/jo0258249

M3 - Article

C2 - 12126407

AN - SCOPUS:0037178495

SN - 0022-3263

VL - 67

SP - 5202

EP - 5207

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 15

ER -

A simple and versatile method for the synthesis of acetals from aldehydes and ketones using bismuth triflate

Abstract

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this