Hydrochloric Acid → 52119-56-9

HRID 2083113Notes

Reaction equation

HRID 2083113 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].Cl.[CH2:22](Br)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>CS(C)=O>[C:11]([C:7]1[CH:8]=[C:9]([CH:10]=[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[C:6]=1[OH:15])[C:18]([S:20][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[S:19])([CH3:14])([CH3:13])[CH3:12]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 6348Carbon DisulfideHCID 7498Benzyl BromideHCID 14797Potassium HydroxideHCID 314052,6-Di-tert-butylphenol

Product 1

HCID 32499852119-56-9

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
10 °C

Procedure

A flask was charged with 0.3 mol of 2,6-di-t-butylphenol and 150 ml of dimethylsulfoxide. To the flask, maintained at 10° C., was added dropwise an aqueous solution of 0.6 mol potassium hydroxide, followed by 0.3 mol carbon disulfide. The resulting reaction mixture was stirred at 10° C. for 1 hour and then allowed to warm to about 25° C. Concentrated hydrochloric acid (0.3 mol) was then added slowly to the reaction mixture, maintained at 0° C. Benzylbromide (0.3 mol) was then added and the reaction mixture heated at 50° C. for 1 hour. The reaction mixture was cooled, diluted with 600 ml ice water, and extracted with ether. The ether extracts were washed with water, dried over magnesium sulfate and evaporated to give the crude product. After recrystallization from hexane, the product melted at 110°-112° C. Elemental analysis of the product is tabulated in Table I. The product is believed to be novel.

Workup

  1. customThe resulting reaction mixture
  2. temperatureto warm to about 25° C
  3. temperaturemaintained at 0° C
  4. temperaturethe reaction mixture heated at 50° C. for 1 hour
  5. temperatureThe reaction mixture was cooled
  6. extractionextracted with ether
  7. washThe ether extracts were washed with water
  8. dry with materialdried over magnesium sulfate
  9. customevaporated

Sources & evidence

ORD record
ord-826cf6893c544698a4e9452f8611d06d
Source dataset
uspto-grants-1978_04
Patent number
US04083989

Reaction notes

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