Benzene → HCID 54167029, compound

HRID 359738Notes

Reaction equation

HRID 359738 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

4

Reactant 3

HCID 241BenzeneHCID 70670Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl esterHCID 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.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 20 hours
  3. concentrationconcentrated in vacuo to an oil

Sources & evidence

ORD record
ord-3eb3cc59e7d44a31ab3dd34db094d0a5
Source dataset
uspto-grants-1991_03
Patent number
US05002967

Reaction notes

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