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

HRID 841560Notes

Reaction equation

HRID 841560 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH2:7][CH2:8][CH2:9][C:10]2([CH3:14])[CH3:13])=[CH:5][CH:4]=1.C(O)(=[O:17])C>O.[O-2].[O-2].[O-2].[Cr+6]>[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6](=[CH:5][CH:4]=1)[C:7](=[O:17])[CH2:8][CH2:9][C:10]2([CH3:14])[CH3:13]

Participants

5

Reactant 2

HCID 176Acetic Acid2×HCID 124151467-Methoxy-1,1-dimethyl-1,2,3,4-tetrahydronaphthalene2×

Product 1

HCID 124151476-Methoxy-4,4-dimethyl-3,4-dihydronaphthalen-1(2H)-oneYield 93%

Reagents, catalysts & solvents 2

HCID 10219390chromium (VI) trioxideCatalystHCID 962WaterSolvent2×

Procedure

A solution of 7-methoxy-1,1-dimethyl-1,2,3,4-tetrahydronaphthalene (Intermediate 8, 1.65 g, 8.7 mmol) in 7.5 mL of glacial acetic acid was cooled to 0° C. and treated with a solution of chromium trioxide (2 g, 20 mmol) in 8 mL of acetic acid and 7 mL of water. The reaction mixture was then allowed to warm to ambient temperature and stirred overnight. It was diluted with water and extracted with diethyl ether (×2). The combined organic phase was washed with water (×1), saturated aqueous sodium bicarbonate (×1) and brine (×1), dried over anhydrous magnesium sulfate, filtered and evaporated in vacuo to afford the title compound (1.64 g, 93%) as a yellow oil.

Workup

  1. extractionextracted with diethyl ether (×2)
  2. washThe combined organic phase was washed with water (×1), saturated aqueous sodium bicarbonate (×1) and brine (×1)
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-cd94a92b1c004d41829f84f5f78e382c
Source dataset
uspto-grants-2002_04
Patent number
US06369261B1

Reaction notes

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