Crotonic Acid → 1,3-Bis-(4-benzoyl-3-hydroxyphenoxy)-prop-2-yl crotonate

HRID 621665

Reaction equation

HRID 621665 reaction equation
[C:1]([C:9]1[CH:35]=[CH:34][C:12]([O:13][CH2:14][CH:15]([OH:33])[CH2:16][O:17][C:18]2[CH:23]=[CH:22][C:21]([C:24](=[O:31])[C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)=[C:20]([OH:32])[CH:19]=2)=[CH:11][C:10]=1[OH:36])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:37](O)(=[O:41])/[CH:38]=[CH:39]/[CH3:40]>>[C:37]([O:33][CH:15]([CH2:14][O:13][C:12]1[CH:34]=[CH:35][C:9]([C:1](=[O:8])[C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[C:10]([OH:36])[CH:11]=1)[CH2:16][O:17][C:18]1[CH:23]=[CH:22][C:21]([C:24](=[O:31])[C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)=[C:20]([OH:32])[CH:19]=1)(=[O:41])/[CH:38]=[CH:39]/[CH3:40]

Participants

3

Reactant 2

HCID 637090Crotonic AcidHCID 12422352,2''-Dihydroxy-4,4''-(2-hydroxy-propane-1,3-diyldioxy)dibenzophenone

Product 1

HCID 703950051,3-Bis-(4-benzoyl-3-hydroxyphenoxy)-prop-2-yl crotonateYield 75.1%

Procedure

97 g (0.2 mole) of 1,3-bis-(4-benzoyl-3-hydroxyphenoxy)-2-propanol were esterified analogously to Example 1 with 103 g (1.2 moles) of crotonic acid. After crystallization from an acetone/ethanol mixture (ratio by volume 1:2), 83 g (75 percent of theory) of 1,3-bis-(4-benzoyl-3-hydroxyphenoxy)-prop-2-yl crotonate were obtained in the form of fine white crystals having a melting point of 99° to 103° C. and a purity of 99 percent (HPLC). The structure of the compound obtained was confirmed by UV, IR and NMR spectra.

Workup

  1. customAfter crystallization from an acetone/ethanol mixture (ratio by volume 1:2)

Sources & evidence

ORD record
ord-c9e574ae262349eb8989caac247896ee
Source dataset
uspto-grants-1989_04
Patent number
US04824892

Linked notes

Loading…