6-Methoxy-4,4-dimethyl-3,4-dihydronaphthalen-1(2H)-one → 6-hydroxy-4,4-dimethyl-3,4-dihydronaphthalen-1(2H)-one

HRID 1935766Notes

Reaction equation

HRID 1935766 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9](=[O:13])[CH2:8][CH2:7][C:6]2([CH3:15])[CH3:14]>B(Br)(Br)Br>[OH:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9](=[O:13])[CH2:8][CH2:7][C:6]2([CH3:15])[CH3:14]

Participants

3

Reactant 1

HCID 124151476-Methoxy-4,4-dimethyl-3,4-dihydronaphthalen-1(2H)-one2×

Product 1

HCID 134122536-hydroxy-4,4-dimethyl-3,4-dihydronaphthalen-1(2H)-oneYield 52.6%

Reagents, catalysts & solvents 1

HCID 25134Boron tribromideSolvent

Procedure

A stirred, cooled (−78° C.) solution of 6-methoxy-4,4-dimethyl-1,2,3,4-tetrahydronaphthalene-1-one (Intermediate 9, 0.8, 3 mmol) under argon was treated with a 1M solution of boron tribromide (10 mL). The reaction mixture was allowed to warm to ambient temperature and stirred overnight. The reaction mixture was cooled to −78° C., quenched and diluted with saturated aqueous sodium bicarbonate solution and the aqueous phase was extracted with dichloromethane (×2). The combined organic phase was dried over anhydrous sodium sulfate, filtered and evaporated in vacuo to an oil. Flash column chromatography over silica gel (230-400 mesh) using 30% ethyl acetate in hexane as the eluent afforded the title compound (0.3 g, 52%) as a yellow viscous oil.

Workup

  1. temperatureThe reaction mixture was cooled to −78° C.
  2. customquenched
  3. additiondiluted with saturated aqueous sodium bicarbonate solution
  4. extractionthe aqueous phase was extracted with dichloromethane (×2)
  5. dry with materialThe combined organic phase was dried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. customevaporated in vacuo to an oil

Sources & evidence

ORD record
ord-361271b84603479082b35ab32729ecc4
Source dataset
uspto-grants-2002_05
Patent number
US06387892B1

Reaction notes

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