Ethyl 4-formylbenzoate → p-[(E)-2-(1,1,3,3-tetramethyl-5-indanyl)propenyl]-benzoic acid ethyl ester

HRID 2286084Notes

Reaction equation

[Br-].[CH3:2][C:3]1([CH3:35])[C:11]2[C:6](=[CH:7][C:8]([CH:12]([P+](C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[CH3:13])=[CH:9][CH:10]=2)[C:5]([CH3:34])([CH3:33])[CH2:4]1.[CH2:36]([O:38][C:39]([C:41]1[CH:48]=[CH:47][C:44]([CH:45]=O)=[CH:43][CH:42]=1)=[O:40])[CH3:37]>C1OCCC1>[CH2:36]([O:38][C:39](=[O:40])[C:41]1[CH:48]=[CH:47][C:44](/[CH:45]=[C:12](/[C:8]2[CH:7]=[C:6]3[C:11](=[CH:10][CH:9]=2)[C:3]([CH3:35])([CH3:2])[CH2:4][C:5]3([CH3:33])[CH3:34])\[CH3:13])=[CH:43][CH:42]=1)[CH3:37]

Participants

Conditions

Temperature: 65 °C

Procedure

300 ml of butylene oxide are added to 30.5 g of [1-(1,1,3,3-tetramethyl-5-indanyl)ethyl]-triphenylphosphonium bromide and 8 g of 4-ethoxycarbonylbenzaldehyde and the mixture is then stirred at 65° C. for 12 hours in an inert gas atmosphere. The resulting clear solution is cooled, introduced into ca 500 ml of ice/water and extracted twice with hexane. The organic extract is extracted three times with methanol/water, dried over sodium sulphate and concentreated under reduced pressure. The residue is purified by adsorption on silica gel using hexane/ether (19:1) for the elution. The p-[(E)-2-(1,1,3,3-tetramethyl-5-indanyl)propenyl]-benzoic acid ethyl ester obtained from the eluate melts at 70°-71° C. after recrystallization from ether/hexane.

Workup

temperatureThe resulting clear solution is cooled
extractionextracted twice with hexane
extractionThe organic extract
extractionis extracted three times with methanol/water
dry with materialdried over sodium sulphate
customThe residue is purified by adsorption on silica gel
washfor the elution

Sources & evidence

ORD record: ord-ad649481652a4d8fbfe5885b51b12d99
Source dataset: uspto-grants-1982_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04326055

Reaction notes

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