Hydrochloric Acid → HCID 19577118, compound

HRID 1643235Notes

Reaction equation

HRID 1643235 reaction equation
[C:1]([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])[CH3:2].[C:17]1(=O)[CH2:21][CH2:20][CH2:19][CH2:18]1.Cl>CO>[C:1]([C:5]1[CH:10]=[C:9]([S:11][C:17]2([S:11][C:9]3[CH:8]=[C:7]([C:12]([CH3:13])([CH3:14])[CH3:15])[C:6]([OH:16])=[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[CH:10]=3)[CH2:21][CH2:20][CH2:19][CH2:18]2)[CH:8]=[C:7]([C:12]([CH3:15])([CH3:14])[CH3:13])[C:6]=1[OH:16])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 8452CyclopentanoneHCID 703702,6-Di-tert-butyl-4-mercaptophenol

Product 1

HCID 19577118HCID 19577118, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 2,6-di-t-butyl-4-mercaptophenol (600 mg, 1.04 mmol) in methanol (10 mL) was added cyclopentanone (1.5 mL) and a catalytic amount of concentrated hydrochloric acid. The mixture was heated and stirred at 60° C. overnight. The solvent was distilled off from the reaction mixture, and the resulting residue was purified by a flash column chromatography (filler: manufactured by Kanto Kagaku, K.K., 60Nmesh40-100, developing solvent:n-hexane/ethyl acetate (volume ratio)=1/0 to 100/1) to give bis(3,5-di-t-butyl-4-hydroxyphenylthio)cyclopentane (yield 485 mg and 67%).

Workup

  1. temperatureThe mixture was heated
  2. distillationThe solvent was distilled off from the reaction mixture
  3. customthe resulting residue was purified by a flash column chromatography (filler: manufactured by Kanto Kagaku, K.K., 60Nmesh40-100, developing solvent:n-hexane/ethyl acetate (volume ratio)=1/0 to 100/1)

Sources & evidence

ORD record
ord-c76ffbe7fe184d06b9de32032e617aad
Source dataset
uspto-grants-2012_02
Patent number
US08119686B2

Reaction notes

Loading…