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

HRID 1722795Notes

Reaction equation

HRID 1722795 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

2,6-bis(1,1-Dimethylethyl)-4-mercaptophenol (36.4 g, 0.15 mole) was dissolved in methanol (250 ml) in a 1 liter, round bottom, 3-necked flask equipped with a stirrer, gas inlet and gas outlet. The solution was flushed with argon and freshly distilled acrolein (25 g, 0.45 mole) and triethylamine (2.4 ml) were added dropwise over a one hour period and the solvent was evaporated on a rotary evaporator and the product purified by chromatography over silica, m.p. ca. 64°-65° C. Analysis calc. for C17H26O2S(294.45)

Workup

  1. customround bottom, 3-necked flask equipped with a stirrer, gas inlet and gas outlet
  2. additionwere added dropwise over a one hour period
  3. customthe solvent was evaporated on a rotary evaporator
  4. customthe product purified by chromatography over silica, m.p. ca. 64°-65° C

Sources & evidence

ORD record
ord-e99aaecf3fd346c98b4d2c0203820f15
Source dataset
uspto-grants-1989_08
Patent number
US04857558

Reaction notes

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