Carbon Disulfide → 52119-95-6

HRID 1461678Notes

Reaction equation

HRID 1461678 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×

Conditions

Temperature
22.5 °C

Procedure

The ditalow amine salt of 4-hydroxy -3, 5-di-tert-butyldithiobenzoic acid was prepared as follows: 2,6-di-tert-butyl phenol (20.6 g) was dissolved in dimethylsulphoxide (60 cm3). To this well stirred solution under nitrogen was added KOH (5.6 g) dissolved in the minimum amount of water. After the addition was completed, CS2 (7.6 g) was run in maintaining the temperature between 20-25° C. The mixture was maintained at this temperature for one hour, at 60° C. for two hours and then cooled and poured into water (250 cm3). After acidification (10% HCl), extraction into diethylether and drying over Na2SO4 the product was isolated by roto-evaporation (calculated for C15H22OS2, C=63.83 wt. % and H=7.80 wt. %; found C=63.65 wt. % and H=7.86 wt. %).

Workup

  1. additionAfter the addition
  2. temperatureThe mixture was maintained at this temperature for one hour, at 60° C. for two hours
  3. temperaturecooled
  4. extractionAfter acidification (10% HCl), extraction into diethylether
  5. dry with materialdrying over Na2SO4 the product
  6. customwas isolated by roto-evaporation (calculated for C15H22OS2, C=63.83 wt. % and H=7.80 wt. %; found C=63.65 wt. % and H=7.86 wt. %)

Sources & evidence

ORD record
ord-ef1a83767ea24495b5e8994c87d988e7
Source dataset
uspto-grants-1991_12
Patent number
US05076945

Reaction notes

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