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

HRID 1110511Notes

Reaction equation

HRID 1110511 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. Anal. Calculated from C19H16Cl2O2 : C, 65.72; H, 4.64; Cl. 20.42 Found: C, 65.75; H, 4.67; Cl, 20.16.

Workup

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

Sources & evidence

ORD record
ord-78acfe862da243518965458b2f7311fb
Source dataset
uspto-grants-1990_12
Patent number
US04975438

Reaction notes

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