Dichloromethane → 3-(Methoxymethoxy)benzaldehyde

HRID 1288109Notes

Reaction equation

HRID 1288109 reaction equation
C(Cl)Cl.[CH3:4][O:5][CH2:6][O:7][CH3:8].[OH2:9].[C:10]1([CH3:20])[CH:15]=[CH:14][C:13](S(O)(=O)=O)=C[CH:11]=1>C(N(CC)CC)C>[CH3:4][O:5][CH2:6][O:7][C:8]1[CH:11]=[C:10]([CH:15]=[CH:14][CH:13]=1)[CH:20]=[O:9]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 8020DimethoxymethaneHCID 521998p-Toluenesulfonic acid monohydrate

Product 1

HCID 122735133-(Methoxymethoxy)benzaldehydeYield 60%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

m-Hydroxybenzaldehyde (32 g., 0.25 moles) methylene chloride (500 ml.), dimethoxymethane (100 ml., 1.13 moles), and p-toluenesulfonic acid monohydrate (250 mg.) were refluxed overnight under nitrogen using a Soxhlet extractor containing type 3A molecular sieves (150 g.). The reaction mixture was allowed to cool treated with triethylamine (2 ml.) to neutralize the acid catalyst and washed with 1N NaOH (2 × 200 ml.), water and dried (Na2SO4). Evaporation of solvent afforded a 28 g. residue, which after distillation, b.p. 92°-105° at 0.7 - 0.8 mm. gave 24.6 g. of m-methoxymethoxybenzaldehyde, (60% yield).

Workup

  1. temperatureto cool
  2. washwashed with 1N NaOH (2 × 200 ml.), water
  3. dry with materialdried (Na2SO4)
  4. customEvaporation of solvent
  5. customafforded a 28 g
  6. distillationresidue, which after distillation, b.p. 92°-105° at 0.7 - 0.8 mm
  7. customgave 24.6 g

Sources & evidence

ORD record
ord-1de75db3dbba42e190868ff949a627d2
Source dataset
uspto-grants-1976_10
Patent number
US03987105

Reaction notes

Loading…