Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl ester → (E)-5,5-bis(4-chlorophenyl)-2,4-pentadienoic acid ethyl ester

HRID 2232759Notes

Reaction equation

HRID 2232759 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=2)=[CH:9][CH:10]=O)=[CH:4][CH:3]=1.[C:19]([CH:24]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([O:21][CH2:22][CH3:23])=[O:20]>C(O)C>[CH2:22]([O:21][C:19](=[O:20])/[CH:24]=[CH:10]/[CH:9]=[C:8]([C:12]1[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=1)[C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=1)[CH3:23]

Participants

4

Reactant 2

HCID 70670Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl esterHCID 145472283,3-Bis(4-chlorophenyl)prop-2-enal

Product 1

HCID 14347256(E)-5,5-bis(4-chlorophenyl)-2,4-pentadienoic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

As in Example 99, 3,3-bis(4-chlorophenyl)-2-propenal (11.08) was reacted with (carbethoxymethylene)triphenylphosphorane (14.3 g) in ethanol (30 ml) for 30 minutes at ambient temperature. The mixture of esters obtained from the usual work up was purified by crystallization from ether-hexane to give 8.1 g of (E)-5,5-bis(4-chlorophenyl)-2,4-pentadienoic acid ethyl ester, mp 98°-100° C. A portion of the (E)-isomer was crystallized from hexane to yield the pure ester (E)-5,5-bis(4-chlorophenyl)-2,4-pentadienoic acid ethyl ester mp 98.5°-100° C.

Workup

  1. customobtained from the usual work
  2. customup was purified by crystallization from ether-hexane

Sources & evidence

ORD record
ord-2a84c5ab77af48e9b8d0095f881ba609
Source dataset
uspto-grants-1988_11
Patent number
US04788206

Reaction notes

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