Benzene → HCID 54167029, compound

Reaction equation

[CH3:1][C:2]([C:5]1[CH:6]=[C:7]([S:16][CH2:17][CH2:18]C=O)[CH:8]=[C:9]([C:12]([CH3:15])([CH3:14])[CH3:13])[C:10]=1[OH:11])([CH3:4])[CH3:3].[C:21]([CH:26]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([O:23][CH2:24][CH3:25])=[O:22].[CH:46]1C=CC=CC=1>>[CH3:14][C:12]([C:9]1[CH:8]=[C:7]([S:16][CH2:17][CH2:18][CH:46]=[CH:26][C:21]([O:23][CH2:24][CH3:25])=[O:22])[CH:6]=[C:5]([C:2]([CH3:4])([CH3:1])[CH3:3])[C:10]=1[OH:11])([CH3:15])[CH3:13]

Participants

Reactant 3

HCID 241Benzene

HCID 70670Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl ester

HCID 140118163-[[3,5-Bis(1,1-dimethylethyl)-4-hydroxyphenyl]thio]propanal

Product 1

HCID 54167029HCID 54167029, compound

Procedure

Triethylamine (1.1 ml, 7.6 mmole) was added to a solution of 2,6-bis(1,1-dimethylethyl)-4-mercaptophenol (18.2 g, 76 mmole) in methanol (200 ml) and stirred for 30 minutes. Freshly distilled acrolein (12.8 g, 0.23 mole) was added and the solution stirred at room temperature. Chromatography on silica gave 3-[[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]thio]propanal. To a solution of the aldehyde (2.0 g, 6.8 mmole) in benzene (20 ml) under argon was added in one portion (carbethoxymethylene)triphenylphosphorane (2.36 g, 6.8 mmole). The mixture was heated at reflux for 20 hours, allowed to stand at room temperature for three days, and then concentrated in vacuo to an oil. Chromatography on silica gel gave the title compound.