Water → 3,4-Dihydro-4,4-dimethyl-1(carboethoxymethyl)-6-acetyl-naphthalene

HRID 2085855Notes

Reaction equation

HRID 2085855 reaction equation
[CH3:1][C:2]1([C:7]2[CH:8]=[C:9]3[C:14](=[CH:15][CH:16]=2)[C:13](O)([CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH2:12][CH2:11][C:10]3([CH3:25])[CH3:24])OCC[O:3]1.CC1C=CC(S(O)(=O)=O)=CC=1.O>C1C=CC=CC=1>[CH3:24][C:10]1([CH3:25])[C:9]2[C:14](=[CH:15][CH:16]=[C:7]([C:2](=[O:3])[CH3:1])[CH:8]=2)[C:13]([CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:12][CH2:11]1

Participants

5

Reactant 3

HCID 962WaterHCID 6101p-Toluenesulfonic acidHCID 18415063(+/-) 6-(2-Methyl-1,3-dioxolan-2-yl)-1,2,3,4-tetrahydro-4,4-dimethyl-1-hydroxy-1-(carboethoxymethyl)-naphthalene

Product 1

HCID 225715193,4-Dihydro-4,4-dimethyl-1(carboethoxymethyl)-6-acetyl-naphthalene

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A solution of (+/−) 6-(2-methyl-1,3-dioxolan-2-yl)-1,2,3,4-tetrahydro-4,4-dimethyl-1-hydroxy-1-(carboethoxymethyl)-naphthlene ((Compound D16, 321 mg, 0.90 mmol) and catalytic amount of TsOH in 20 ml of benzene was refluxed for 12 h. During the reaction the water generated from the reaction was periodically removed by a Dean-Stark trap. The solvent was removed and the residue was purified by column chromatography (silica, ethyl acetate/hexane (1/3)) to give the title compound as an oil (215 mg).

Workup

  1. customwas periodically removed by a Dean-Stark trap
  2. customThe solvent was removed
  3. customthe residue was purified by column chromatography (silica, ethyl acetate/hexane (1/3))

Sources & evidence

ORD record
ord-61a3d7721593446789f304374d6c19ff
Source dataset
uspto-grants-2004_04
Patent number
US06720425B2

Reaction notes

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