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

HRID 986308Notes

Reaction equation

HRID 986308 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, 0.0076 mole) was added to a solution of 2,6-bis(1,1-dimethylethyl)-4-mercaptophenol (18.2 g, 0.076 mole) in methyl alcohol (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. The product was purified by chromatography on silica and characterized by its NMR and IR spectra and m.p. ca. 75° C.

Workup

  1. stirringthe solution stirred at room temperature
  2. customThe product was purified by chromatography on silica

Sources & evidence

ORD record
ord-3a00670d4f3d47d1832fac4a2a9d178a
Source dataset
uspto-grants-1987_12
Patent number
US04711903

Reaction notes

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