(2-Methoxymethoxyphenyl)(2-hydroxy-3-methoxyphenyl)methane → (2-Hydroxyphenyl)-(2-hydroxy-3-methoxyphenyl)methane

HRID 1111284Notes

Reaction equation

HRID 1111284 reaction equation
COC[O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([O:18][CH3:19])[C:13]=1[OH:20]>CO.C1(C)C=CC(S(O)(=O)=O)=CC=1>[OH:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([O:18][CH3:19])[C:13]=1[OH:20]

Participants

4

Reactant 1

HCID 22151955(2-Methoxymethoxyphenyl)(2-hydroxy-3-methoxyphenyl)methane

Product 1

HCID 22151938(2-Hydroxyphenyl)-(2-hydroxy-3-methoxyphenyl)methane

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6101p-Toluenesulfonic acidSolvent

Procedure

(2-Methoxymethoxyphenyl)(2-hydroxy-3-methoxyphenyl)methane (3.95 g, 14 mmol) was dissolved in 150 ml of methanol containing 0.026 g of p-toluene sulfonic acid and the mixture was heated at reflux overnight. The volatiles were then removed by evaporation under reduced pressure and the solid that remained was taken up in ether. The ethereal solution was extracted with saturated aqueous sodium bicarbonate, dried over magnesium sulfate, and concentrated by evaporation under reduced pressure. The white solid residue was dried to obtain 3.66 g (99 percent of theory) of the title compound. The proton nmr spectrum was consistent with the assigned structure.

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux overnight
  3. customThe volatiles were then removed by evaporation under reduced pressure
  4. extractionThe ethereal solution was extracted with saturated aqueous sodium bicarbonate
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated by evaporation under reduced pressure
  7. customThe white solid residue was dried

Sources & evidence

ORD record
ord-7cc9218b24b64759b0de983cd1e053d4
Source dataset
uspto-grants-1990_12
Patent number
US04979978

Reaction notes

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