Acrolein → 3-[[3,5-Bis(1,1-dimethylethyl)-4-hydroxyphenyl]thio]propanal

HRID 359737Notes

Reaction equation

HRID 359737 reaction equation
C(N(CC)CC)C.[CH3:8][C:9]([C:12]1[CH:17]=[C:16]([SH:18])[CH:15]=[C:14]([C:19]([CH3:22])([CH3:21])[CH3:20])[C:13]=1[OH:23])([CH3:11])[CH3:10].[CH:24]([CH:26]=[CH2:27])=[O:25]>CO>[CH3:11][C:9]([C:12]1[CH:17]=[C:16]([S:18][CH2:27][CH2:26][CH:24]=[O:25])[CH:15]=[C:14]([C:19]([CH3:22])([CH3:21])[CH3:20])[C:13]=1[OH:23])([CH3:8])[CH3:10]

Participants

5

Reactant 3

HCID 7847AcroleinHCID 8471TriethylamineHCID 703702,6-Di-tert-butyl-4-mercaptophenol

Product 1

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

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

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.

Workup

  1. stirringthe solution stirred at room temperature

Sources & evidence

ORD record
ord-dfd48cbaef954f8b9c34ee304addff70
Source dataset
uspto-grants-1991_03
Patent number
US05002967

Reaction notes

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