Hydrochloric Acid → 3',5'-Bis(tert-butyl)-4'-hydroxyacetophenone

HRID 2947

Reaction equation

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

Participants

Conditions

Temperature: -4 °C

Procedure

Under a nitrogen atmosphere, 6.89 ml of acetylchloride and 14.75 ml of stannic chloride were dissolved in 200 ml of methylene chloride and chilled to -4° C. To this was added 20 g of 2,6-di-t-butylphenol (in 100 ml of methylene chloride) over 10 minutes. The resultant mixture was stirred for 30 minutes at 0° C., then poured into a mixture of 400 ml of ice and 1N hydrochloric acid and stirred. The mixture separated into layers which were subsequently separated. The organic layer was washed with 100 ml of saturated sodium bicarbonate and 100 ml of brine. The organic layer was dried and the solvent evaporated to give 23.39 g of the desired subtitled intermediate.

Workup

customThe mixture separated into layers which
customwere subsequently separated
washThe organic layer was washed with 100 ml of saturated sodium bicarbonate and 100 ml of brine
customThe organic layer was dried
customthe solvent evaporated

Sources & evidence

ORD record: ord-5ea8ac69bd1848ae813a64e74a7a7adf
Source dataset: uspto-grants-1998_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05731336

Linked notes

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