Water → HCID 53735088, compound

HRID 1953889Notes

Reaction equation

HRID 1953889 reaction equation
C[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](OCC)=O)[CH2:12][CH2:11][C:10]3([CH3:25])[CH3:24])[O:6][CH2:5][CH2:4][O:3]1.[CH3:26][C:27]1C=CC(S(O)(=O)=O)=CC=1.[OH2:37]>C1C=CC=CC=1>[CH3:24][C:10]1([CH3:25])[C:9]2[C:14](=[CH:13][CH:17]=[C:18]([C:26](=[O:37])[CH3:27])[CH:8]=2)[C:15]([CH2:16][CH2:7][C:2]([O:3][CH2:4][CH3:5])=[O:6])=[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 53735088HCID 53735088, compound

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-91ea153792ac46aab08c71dc406cedc1
Source dataset
uspto-grants-2000_09
Patent number
US06117987

Reaction notes

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