p-Toluenesulfonic acid → 1-(2-Hydroxy-3,4-dimethoxyphenyl)-1-(2-hydroxyphenyl)cyclopropane

HRID 359202Notes

Reaction equation

HRID 359202 reaction equation
COC[O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[C:11]1([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[C:16]([O:22][CH3:23])[C:15]=2[O:24]COC)[CH2:13][CH2:12]1.C1(C)C=CC(S(O)(=O)=O)=CC=1>CO>[OH:24][C:15]1[C:16]([O:22][CH3:23])=[C:17]([O:20][CH3:21])[CH:18]=[CH:19][C:14]=1[C:11]1([C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[OH:4])[CH2:12][CH2:13]1

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 198126851-(2-Methoxymethoxyphenyl)-1-(3,4-dimethoxy-2-methoxymethoxyphenyl)cyclopropane

Product 1

HCID 198126861-(2-Hydroxy-3,4-dimethoxyphenyl)-1-(2-hydroxyphenyl)cyclopropaneYield 99.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 1.16 g (3.1 mmol) of 1-(2-methoxymethoxyphenyl)-1-(3,4-dimethoxy-2-methoxymethoxyphenyl)cyclopropane and 80 mg (0.47 mmol) of p-toluenesulfonic acid in 26 ml of methanol was heated at reflux with stirring for 2 hours under an argon atmosphere. The mixture was concentrated to half by evaporation under reduced pressure and 40 ml of ether was added. The resulting solution was extracted with 30 ml of 5 percent aqueous sodium bicarbonate then 30 ml of water, dried over magnesium sulfate, and concentrated by evaporation under reduced pressure to obtain 880 mg of the title compound as a foamy oil. The proton NMR spectrum was consistent with the assigned structure.

Workup

  1. temperatureat reflux
  2. concentrationThe mixture was concentrated to half by evaporation under reduced pressure and 40 ml of ether
  3. additionwas added
  4. extractionThe resulting solution was extracted with 30 ml of 5 percent aqueous sodium bicarbonate
  5. dry with material30 ml of water, dried over magnesium sulfate
  6. concentrationconcentrated by evaporation under reduced pressure

Sources & evidence

ORD record
ord-1e3016536fae48cd9df58f13665023e6
Source dataset
uspto-grants-1991_03
Patent number
US04999448

Reaction notes

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