Catechol → 2-(3-Methoxypropyloxy)-phenol

HRID 264924Notes

Reaction equation

HRID 264924 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 dimethylformamide is added at room temperature, within a period of 30 minutes, to a suspension of 8.4 g of NaH (60% dispersion in mineral oil) in 300 ml of dimethylformamide, and the mixture is stirred for one hour at room temperature. A solution of 49.3 g of 3-bromopropyl methyl ether in 80 ml of dimethylformamide is then added dropwise. The reaction mixture is stirred for a further 80 hours at room temperature and is then concentrated by evaporation under reduced pressure at a bath temperature of 30° C. The residue is partitioned between diethyl ether and water. The combined organic phases are dried over magnesium sulfate and concentrated by evaporation, and the residue is purified by FC (100 g of silica gel, hexane/dichloromethane=5:95), yielding the title compound: Rf (dichloromethane/diethyl ether=96:4)=0.35; HPLC Rt =11.2 minutes.

Workup

  1. stirringThe reaction mixture is stirred for a further 80 hours at room temperature
  2. concentrationis then concentrated 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 materialThe combined organic phases are dried over magnesium sulfate
  5. concentrationconcentrated by evaporation
  6. customthe residue is purified by FC (100 g of silica gel, hexane/dichloromethane=5:95)

Sources & evidence

ORD record
ord-f5891857c7904226a1400edbc6adebce
Source dataset
uspto-grants-1997_07
Patent number
US05646143

Reaction notes

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