Catechol → 2-(3-Methoxypropyloxy)-phenol

HRID 1452122Notes

Reaction equation

HRID 1452122 reaction equation
[C:1]1([C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[OH:4])[OH:2].[H-].[Na+].[CH3:11][O:12][CH2:13][CH2:14][CH2:15]Br>CN(C)C=O>[CH3:11][O:12][CH2:13][CH2:14][CH2:15][O:2][C:1]1[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=1[OH:4]

Participants

5

Reactant 3

HCID 289CatecholHCID 24758Sodium hydrideHCID 5245511-Bromo-3-methoxypropane

Product 1

HCID 214586242-(3-Methoxypropyloxy)-phenol

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

A solution of 22 g of pyrocatechol in 80 ml of N,N-dimethylformamide is added at room temperature in the course of 30 minutes to a suspension of 8.4 g of sodium hydride (60% dispersion in mineral oil) in 300 ml of dimethylformamide, and the reaction mixture is stirred for 1 hour at room temperature. A solution of 49.3 g of 3-bromopropyl methyl ether in 80 ml of dimethylformamide is then added dropwise thereto. The reaction mixture is stirred further for 80 hours at room temperature and then concentrated by evaporation under reduced pressure at a bath temperature of 30° C. The residue is partitioned between diethyl ether and water. The organic phases are combined, dried over magnesium sulfate and concentrated by evaporation and the residue is purified by means of FC (100 g of silica gel, hexane/dichloromethane 5:95) to yield the title compound: Rf (dichloromethane/diethyl ether 96:4)=0.35; HPLC Rt =11.2 minutes.

Workup

  1. stirringThe reaction mixture is stirred further for 80 hours at room temperature
  2. concentrationconcentrated by evaporation under reduced pressure at a bath temperature of 30° C
  3. customThe residue is partitioned between diethyl ether and water
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated by evaporation
  6. customthe residue is purified by means of FC (100 g of silica gel, hexane/dichloromethane 5:95)

Sources & evidence

ORD record
ord-8719b4ee5b7947fb8877056c34340018
Source dataset
uspto-grants-1997_02
Patent number
US05606078

Reaction notes

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