Acetic Acid → 2-[(3,5-Dimethoxyphenyl)methoxy]phenol

HRID 1976209Notes

Reaction equation

HRID 1976209 reaction equation
[OH-].[K+].[CH3:3][O:4][C:5]1[CH:6]=[C:7]([CH:27]=[C:28]([O:30][CH3:31])[CH:29]=1)[CH2:8][O:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[O:16]S(C1C=CC(C)=CC=1)(=O)=O.C(O)(=O)C>C(O)C.O>[CH3:31][O:30][C:28]1[CH:27]=[C:7]([CH:6]=[C:5]([O:4][CH3:3])[CH:29]=1)[CH2:8][O:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[OH:16]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 14797Potassium HydroxideHCID 220006591-[3,5-Dimethoxy-benzyloxy]-2-[toluene-4-sulfonyloxy]benzene

Product 1

HCID 220006692-[(3,5-Dimethoxyphenyl)methoxy]phenolYield 75%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A solution of potassium hydroxide (1.75 g, 31.26 mmol) in ethanol (30 cm3, absolute) and water (30 cm3) was added in portions 15 minutes apart to 1-[3,5-dimethoxy-benzyloxy]-2-[toluene-4-sulfonyloxy]benzene (0.68 g, 1.64 mmol). After heating to reflux for 1 hour, the cooled solution was neutralized with glacial acetic acid and evaporated under reduced pressure. The residue was extracted with diethyl ether (3×20 cm3), and the extracts were washed with sodium bicarbonate (40 cm3) and sodium hydroxide (3×20 cm3, 3% aqueous solution). The sodium hydroxide portion was saturated with solid carbon dioxide pellets, and the precipitate was removed by filtration to give the phenol (0.32 g, 74%).

Workup

  1. temperatureAfter heating
  2. temperatureto reflux for 1 hour
  3. customevaporated under reduced pressure
  4. extractionThe residue was extracted with diethyl ether (3×20 cm3)
  5. washthe extracts were washed with sodium bicarbonate (40 cm3) and sodium hydroxide (3×20 cm3, 3% aqueous solution)
  6. customthe precipitate was removed by filtration

Sources & evidence

ORD record
ord-b11ce7e4f23e44cf9aecdbd26395a68e
Source dataset
uspto-grants-2001_05
Patent number
US06225352B1

Reaction notes

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