Water → (2-Methoxy-1-methoxymethyl-ethoxy)-benzene

HRID 636942Notes

Reaction equation

HRID 636942 reaction equation
[CH3:1][O:2][CH2:3][CH:4]([O:8]S(C)(=O)=O)[CH2:5][O:6][CH3:7].[C:13]1(O)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[CH3:1][O:2][CH2:3][CH:4]([CH2:5][O:6][CH3:7])[O:8][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

6

Reactant 4

HCID 962WaterHCID 996PhenolHCID 11430Potassium CarbonateHCID 225957861,3-Dimethoxypropan-2-yl methanesulfonate

Product 1

HCID 22665641(2-Methoxy-1-methoxymethyl-ethoxy)-benzene

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

A stirred mixture of 2.0 g of methanesulfonic acid 2-methoxy-1-methoxymethyl-ethyl ester, 1.4 g of phenol and 2,8 g of powdered potassium carbonate in 50 mL of dry N,N-dimethylformamide was heated at 90° C. for 24 hours. After cooling, water was added at room temperature and the mixture extracted with diethyl ether. The combined ether extracts were washed with aqueous sodium hydroxide (2 N) and water, dried (sodium sulfate) and concentrated. The crude product (1.0 g) was used in the next step without further purification. EI-MS: 198 (M+).

Workup

  1. temperatureAfter cooling
  2. extractionthe mixture extracted with diethyl ether
  3. washThe combined ether extracts were washed with aqueous sodium hydroxide (2 N) and water
  4. dry with materialdried (sodium sulfate)
  5. concentrationconcentrated
  6. customThe crude product (1.0 g) was used in the next step without further purification

Sources & evidence

ORD record
ord-c35e2ce90ed4447f8a6bfef2ce8ddd06
Source dataset
uspto-grants-2001_02
Patent number
US06194409B1

Reaction notes

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