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

HRID 1087588Notes

Reaction equation

HRID 1087588 reaction equation
[CH3:1][C:2]([C:5]1[CH:10]=[C:9]([SH:11])[CH:8]=[C:7]([C:12]([CH3:15])([CH3:14])[CH3:13])[C:6]=1[OH:16])([CH3:4])[CH3:3].[CH:17]([CH:19]=[CH2:20])=[O:18].C(N(CC)CC)C>CO>[CH3:4][C:2]([C:5]1[CH:10]=[C:9]([S:11][CH2:20][CH2:19][CH:17]=[O:18])[CH:8]=[C:7]([C:12]([CH3:15])([CH3:14])[CH3:13])[C:6]=1[OH:16])([CH3:1])[CH3:3]

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

A mixture of 5.0 g of 2,6-bis(1,1-dimethylethyl)-4-mercaptophenol, 4.0 ml of acrolein, 0.5 ml of triethylamine, and 60 ml of methanol was stirred at room temperature for 17 hr. Then the mixture was distilled to dryness under reduced pressure. The residual oil was chromatographed on silica gel. The column was eluted with hexane-ethyl acetate to furnish 3-[[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]-thio]propanal as viscous oil.

Workup

  1. distillationThen the mixture was distilled to dryness under reduced pressure
  2. customThe residual oil was chromatographed on silica gel
  3. washThe column was eluted with hexane-ethyl acetate

Sources & evidence

ORD record
ord-d5405d5b614e430888a73a244d227cbf
Source dataset
uspto-grants-1991_07
Patent number
US05036105

Reaction notes

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