3-Hydroxybenzaldehyde → 3-(Methoxymethoxy)benzaldehyde

HRID 1822729Notes

Reaction equation

HRID 1822729 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[O:6].Cl[CH2:11][O:12][CH3:13].C(N(C(C)C)CC)(C)C>>[CH3:11][O:12][CH2:13][O:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[O:6]

Participants

4

Reactant 3

HCID 1013-HydroxybenzaldehydeHCID 7864Chloromethyl Methyl EtherHCID 81531Diisopropylethylamine

Product 1

HCID 122735133-(Methoxymethoxy)benzaldehyde

Procedure

A solution of 3-hydroxybenzaldehyde (20 g), chloromethylmethyl ether (25 ml) and diisopropylethylamine (114 ml) intetrahydrofuran (300 ml) was stirred at room temperature overnight. To the reaction mixture was added ice water and was extracted with ethyl acetate. The extract was washed with a saturated aqueous solution of sodium bicarbonate, water and a saturated aqueous solution of sodium chloride, successively, dried over anhydrous magnesium sulfate and concentrated. The residue was purified by column chromatography on silica gel (hexane : ethyl acetate =25:1) to give the title compound (23 g) having the following physical data.

Workup

  1. extractionwas extracted with ethyl acetate
  2. washThe extract was washed with a saturated aqueous solution of sodium bicarbonate, water
  3. dry with materiala saturated aqueous solution of sodium chloride, successively, dried over anhydrous magnesium sulfate
  4. concentrationconcentrated
  5. customThe residue was purified by column chromatography on silica gel (hexane : ethyl acetate =25:1)

Sources & evidence

ORD record
ord-97f6f4a658cc4958bf6b6ae1879c86c1
Source dataset
uspto-grants-2006_05
Patent number
US07037914B2

Reaction notes

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