Acetic Acid → 5-methoxy-3,3-dimethyl-1-indanone

HRID 1690689Notes

Reaction equation

HRID 1690689 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[C:10]2[C:6]([CH2:7][CH2:8][C:9]2([CH3:13])[CH3:12])=[CH:5][CH:4]=1.C(O)(=[O:16])C>C(O)(=O)C.O.[O-2].[O-2].[O-2].[Cr+6]>[CH3:1][O:2][C:3]1[CH:11]=[C:10]2[C:6](=[CH:5][CH:4]=1)[C:7](=[O:16])[CH2:8][C:9]2([CH3:13])[CH3:12]

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 12283213HCID 12283213, compound

Product 1

HCID 122832145-methoxy-3,3-dimethyl-1-indanone

Reagents, catalysts & solvents 2

HCID 10219390chromium (VI) trioxideCatalystHCID 21899381Acetic acid--water (1/1)Solvent

Procedure

A solution of 6-methoxy-1,1-dimethyl-indan (1 g, 5.67 mmol) in acetic acid (5 mL) is cooled to 0° C. and treated with a solution of chromium trioxide (1.3 g, 13 mmol) in acetic acid/H2O (5 mL/4 mL). Then the reaction mixture is allowed to warm to ambient temperature and stirred for 3 h. The reaction mixture is diluted and extracted with ethyl acetate (3×20 mL). The combined organic phases are washed with saturated aqueous NaHCO3 and brine and dried over Na2SO4. Evaporation of solvent affords 5-methoxy-3,3-dimethyl-indan-1-one as a yellow oil: ESMS m/z 191.1 (M+H+).

Workup

  1. additionThe reaction mixture is diluted
  2. extractionextracted with ethyl acetate (3×20 mL)
  3. washThe combined organic phases are washed with saturated aqueous NaHCO3 and brine
  4. dry with materialdried over Na2SO4
  5. customEvaporation of solvent

Sources & evidence

ORD record
ord-effc9d69c3454381b5507ede7d37eefb
Source dataset
uspto-grants-2012_04
Patent number
US08153671B2

Reaction notes

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