Dimethylformamide → 2-(Benzyloxy)-4-(methoxymethoxy)benzaldehyde

HRID 1294147Notes

Reaction equation

HRID 1294147 reaction equation
[OH:1][C:2]1[CH:9]=[C:8]([O:10][CH2:11][O:12][CH3:13])[CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].[CH2:14](Br)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[CH2:14]([O:1][C:2]1[CH:9]=[C:8]([O:10][CH2:11][O:12][CH3:13])[CH:7]=[CH:6][C:3]=1[CH:4]=[O:5])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 27550732-Hydroxy-4-(methoxymethoxy)benzaldehyde

Product 1

HCID 178613372-(Benzyloxy)-4-(methoxymethoxy)benzaldehydeYield 99%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 2-hydroxy-4-methoxymethoxybenzaldehyde (17.1 g), benzyl bromide (19.33 g), anhydrous potassium carbonate (13.0 g) and N,N-dimethylformamide (200 mL) was stirred at room temperature for 15 hrs. The reaction mixture was poured into water and extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated. The obtained residue was subjected to silica gel column chromatography to give 2-benzyloxy-4-methoxymethoxybenzaldehyde as a colorless oil (25.3 g, 99%) from a fraction eluted with ethyl acetate-hexane (1:4, v/v).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-a8d8aaf99b3b4970b46ceecd10d3cb26
Source dataset
uspto-grants-2007_07
Patent number
US07238716B2

Reaction notes

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