Efficient preparation of 2-methyl-1,3-dioxolane-2-ethanol and 2-(2-bromoethyl)-2-methyl-1,3-dioxolane from 4-hydroxy-2-butanone

被引：4

作者：

Petroski, RJ ^{[1
]}

机构：

[1] ARS, USDA, REE, Natl Ctr Agr Utilizat Res,Bioact Agents Res Unit, Peoria, IL 61604 USA

来源：

SYNTHETIC COMMUNICATIONS | 2002年 / 32卷 / 03期

关键词：

D O I：

10.1081/SCC-120002130

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

2-Methyl-1,3-dioxolane-2-ethanol was prepared in 90% isolated yield from 4-hydroxy-2-butanone and ethylene glycol using a weak acid catalyst and ethyl acetate as the reaction solvent. 2-(2-Bromoethyl)-2-methyl-1,3-dioxolane was prepared in 75% isolated yield by bromination of 2-Methyl-1,3-dioxolane-2-ethanol with dibromotriphenylphosphorane. The reagent was prepared in situ by titrating triphenylphosphine with bromine at an ice-ethanol bath temperature. The target compounds are useful methyl vinyl ketone equivalents.

引用

页码：449 / 455

页数：7

共 50 条

[1] Efficient preparation of 2-methyl-1,3-dioxolane-2-ethanol and 2-(2-bromoethyl)-2-methyl-1,3-dioxolane from 4-hydroxy-2-butanone.
Petroski, RJ
[J]. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2001, 222 : U97 - U97
[2] TELOMERIZATION OF ETHYLENE WITH 2-METHYL-1,3-DIOXOLANE
NAYANOV, VP
RAKHMANKULOV, DL
ZLOTSKII, SS
TERENTEV, AB
[J]. BULLETIN OF THE ACADEMY OF SCIENCES OF THE USSR DIVISION OF CHEMICAL SCIENCE, 1975, 24 (03): : 518 - 520
[3] Vibrational Satellites and Pseudorotation in 2-Methyl-1,3-dioxolane
M. G. Faizullin
R. V. Galeev
A. Kh. Mamleev
[J]. Russian Journal of Physical Chemistry A, 2018, 92 : 482 - 487
[4] RADICAL REACTIONS OF VINYLTRIMETHYLSILANE WITH 2-METHYL-1,3-DIOXOLANE
MAKAEVA, RM
MUSAVIROV, RS
KRUGLOV, DE
TERENTEV, AN
[J]. BULLETIN OF THE ACADEMY OF SCIENCES OF THE USSR DIVISION OF CHEMICAL SCIENCE, 1986, 35 (07): : 1466 - 1470
[5] Vibrational Satellites and Pseudorotation in 2-Methyl-1,3-dioxolane
Faizullin, M. G.
Galeev, R. V.
Mamleev, A. Kh
[J]. RUSSIAN JOURNAL OF PHYSICAL CHEMISTRY A, 2018, 92 (03) : 482 - 487
[6] AN IMPROVED SYNTHESIS OF 2-(BETA-BROMOETHYL)-2-METHYL-1,3-DIOXOLANE, A USEFUL METHYL VINYL KETONE EQUIVALENT
HSUNG, RP
[J]. SYNTHETIC COMMUNICATIONS, 1990, 20 (08) : 1175 - 1179
[7] CONVENIENT PROCEDURE FOR PREPARING 2-(3-IODOPROPYL)-2-METHYL-1,3-DIOXOLANE
WU, YK
AHLBERG, P
[J]. SYNTHESIS-STUTTGART, 1994, (05): : 463 - 464
[8] SYNTHESIS OF 4-ACETYLPHENYLMETHYLSILANES USING 2-(4-BROMOPHENYL)-2-METHYL-1,3-DIOXOLANE
NEVILLE, RG
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1959, 24 (01): : 111 - 112
[9] ENTHALPIES OF FORMATION OF CYCLIC ACETALS . 1,3-DIOXOLANE,2-METHYL-1,3-DIOXOLANE, AND 2,4-DIMETHYL-1,3-DIOXOLANES
PIHLAJA, K
HEIKKILA, J
[J]. ACTA CHEMICA SCANDINAVICA, 1969, 23 (03): : 1053 - &
[10] RADICAL-ADDITION OF 1,3-DIOXOLANE AND 2-METHYL-1,3-DIOXOLANE TO 1-HEXANE AND DIMETHYLMALEINATE
SAFIEV, OG
KRUGLOV, DE
ZLOTSKII, SS
RAKHMANKULOV, DL
[J]. IZVESTIYA VYSSHIKH UCHEBNYKH ZAVEDENII KHIMIYA I KHIMICHESKAYA TEKHNOLOGIYA, 1985, 28 (07): : 33 - 36

← 1 2 3 4 5 →