Hydrochloric Acid → HCID 136354631, compound

HRID 1288592Notes

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-:16].[K+].[C:18](=[S:20])=S.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]([O:16][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[S:20])([CH3:14])([CH3:13])[CH3:12]

Participants

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 aqeuous 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 addead 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 coold, 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 crystallization 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

customThe resulting reaction mixture
temperatureto warm to about 25° C
temperatureaddead slowly to the reaction mixture, maintained at 0° C
temperaturethe reaction mixture heated at 50° C. for 1 hour
extractionextracted with ether
washThe ether extracts were washed with water
dry with materialdried over magnesium sulfate
customevaporated

Sources & evidence

ORD record: ord-4db7ffd8f88248e4b3e653ae34e54052
Source dataset: uspto-grants-1976_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US03988471

Reaction notes

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