Sodium Hydroxide → N-(3,5-Di-tert-butyl-4-hydroxyphenyl)methanesulfonamide

HRID 597124Notes

Reaction equation

[NH2:1][C:2]1[CH:7]=[C:6]([C:8]([CH3:11])([CH3:10])[CH3:9])[C:5]([OH:12])=[C:4]([C:13]([CH3:16])([CH3:15])[CH3:14])[CH:3]=1.[CH3:17][S:18](Cl)(=[O:20])=[O:19].[OH-].[Na+]>C(Cl)(Cl)Cl>[C:13]([C:4]1[CH:3]=[C:2]([NH:1][S:18]([CH3:17])(=[O:20])=[O:19])[CH:7]=[C:6]([C:8]([CH3:9])([CH3:10])[CH3:11])[C:5]=1[OH:12])([CH3:16])([CH3:15])[CH3:14]

Participants

Conditions

Temperature: 35 °C

Procedure

To a solution of 11.05 grams (0.05 mole) of 4-amino-2,6-di-tert-butylphenol in 60 ml of chloroform was added with stirring 5.75 grams (0.05 mole) of methanesulfonyl chloride over a 5-minute period. The reaction mixture was heated to 35° C for 15 minutes followed by the dropwise addition of 8.0 grams (0.05 mole) of a 25% aqueous sodium hydroxide solution and finally heating at 47° C for 30 minutes. After cooling to room temperature, the chloroform layer was separated, washed with water and dried over 4A Molecular Sieves and filtered. The solvent was removed in vacuo, and the residue was washed with hexane leaving 5.8 grams of a crude pink product. Recrystallization from toluene and again from ethylene dichloride gave 2.7 grams of colorless crystals melting at 149°-151° C. (Compound 2)

Workup

temperaturefinally heating at 47° C for 30 minutes
temperatureAfter cooling to room temperature
customthe chloroform layer was separated
washwashed with water
dry with materialdried over 4A Molecular Sieves
filtrationfiltered
customThe solvent was removed in vacuo
washthe residue was washed with hexane leaving 5.8 grams of a crude pink product
customRecrystallization from toluene

Sources & evidence

ORD record: ord-746521d158d648e1a10ae0e0e447bff9
Source dataset: uspto-grants-1977_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04013621

Reaction notes

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