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

HRID 1008519Notes

Reaction equation

HRID 1008519 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-987dfd4d93334854a6f431fac3bc5581
Source dataset
uspto-grants-2004_09
Patent number
US06797710B2

Reaction notes

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