Carbon Disulfide → 52119-95-6

HRID 1285282Notes

Reaction equation

HRID 1285282 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([C:11]([CH3:14])([CH3:13])[CH3:12])[C:6]=1[OH:15])([CH3:4])([CH3:3])[CH3:2].[OH-].[K+].[C:18](=[S:20])=[S:19]>CS(C)=O.O>[OH:15][C:6]1[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])=[CH:10][C:9]([C:18]([SH:20])=[S:19])=[CH:8][C:7]=1[C:11]([CH3:14])([CH3:13])[CH3:12]

Participants

6

Reactant 3

HCID 6348Carbon DisulfideHCID 14797Potassium HydroxideHCID 314052,6-Di-tert-butylphenol

Product 1

HCID 371148452119-95-6

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent2×

Procedure

The compound 4-hydroxy-3,5-di-tert.-butyl dithiobenzoic acid was prepared by dissolving 2,6-di-tert.-butyl phenol (20.6 g) in dimethylsulfoxide (60 cm3). To this well stirred solution under a nitrogen blanket was added KOH (5.6 g) dissolved in a minimum amount of water. After the addition was completed carbon disulfide (7.6 g) was added while maintaining the temperature between 20°-25° C. The mixture was maintained at this temperature for 1 hour, then at 60° C. for 2 hours, cooled and poured into water (250 cm.3). After acidification (10% HCl), extraction into diethyl ether and drying over Na2SO4 the product was isolated by rotoevaporation.

Workup

  1. additionAfter the addition
  2. additionwas added
  3. temperaturewhile maintaining the temperature between 20°-25° C
  4. temperatureThe mixture was maintained at this temperature for 1 hour
  5. temperaturecooled
  6. extractionAfter acidification (10% HCl), extraction into diethyl ether
  7. dry with materialdrying over Na2SO4 the product
  8. customwas isolated by rotoevaporation

Sources & evidence

ORD record
ord-5e1f48c10bd34671a6a9747cb5c262a2
Source dataset
uspto-grants-1986_01
Patent number
US04566982

Reaction notes

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