4-Hydroxybenzaldehyde → 4-(Ethoxymethoxy)benzaldehyde

HRID 1473726Notes

Reaction equation

HRID 1473726 reaction equation
[CH2:1]([O:3][CH2:4]Cl)[CH3:2].[OH:6][C:7]1[CH:14]=[CH:13][C:10]([CH:11]=[O:12])=[CH:9][CH:8]=1.C(N(CC)CC)C>C1COCC1>[CH2:1]([O:3][CH2:4][O:6][C:7]1[CH:14]=[CH:13][C:10]([CH:11]=[O:12])=[CH:9][CH:8]=1)[CH3:2]

Participants

5

Reactant 3

HCID 1264-HydroxybenzaldehydeHCID 8471TriethylamineHCID 18523Chloromethyl ethyl ether

Product 1

HCID 110952164-(Ethoxymethoxy)benzaldehyde

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of chloromethyl ethyl ether (5.65 g, 0.06 mol) in 20 ml of THF at 0° C. is added to a mixture of 4-hydroxybenzaldehyde (5 g, 0.041 mol) and 12 ml of triethylamine in 30 ml of THF and the mixture is stirred at ambient temperature for 2 hrs. The triethylamine hydrochloride is filtered off and the solvent is evaporated under reduced pressure to give the 4-ethoxymethoxybenzaldehyde in the form of an oil (6.63 g, 90%).

Workup

  1. filtrationThe triethylamine hydrochloride is filtered off
  2. customthe solvent is evaporated under reduced pressure

Sources & evidence

ORD record
ord-1c393cfb3ed6401099a0c5031731339b
Source dataset
uspto-grants-2015_04
Patent number
US09017673B2

Reaction notes

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