Dimethylformamide → HCID 23076398, compound

HRID 2221518Notes

Reaction equation

HRID 2221518 reaction equation
[CH2:1]([O:8][C:9]1[CH:16]=[CH:15][C:12]([CH:13]=[O:14])=[CH:11][C:10]=1[OH:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CN(C)C=O.[H-].[Na+].Cl[CH2:26][O:27][CH3:28]>O>[CH2:1]([O:8][C:9]1[CH:16]=[CH:15][C:12]([CH:13]=[O:14])=[CH:11][C:10]=1[O:17][CH2:26][O:27][CH3:28])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 7864Chloromethyl Methyl EtherHCID 24758Sodium hydrideHCID 5613694-Benzyloxy-3-hydroxybenzaldehyde

Product 1

HCID 23076398HCID 23076398, compoundYield 100.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 4-benzyloxy-3-hydroxybenzaldehyde (27.30 g) and N,N-dimethylformamide (300 mL) was added sodium hydride (60% in oil, 5.28 g) at 0° C., and the mixture was stirred at room temperature for 1 hr. Chloromethylmethyl ether (16.10 g) was added to the reaction mixture and the mixture was further stirred at room temperature for 15 hrs. The reaction mixture was poured into water and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated. The residue was subjected to silica gel column chromatography to give 4-benzyloxy-3-methoxymethoxybenzaldehyde as a colorless oil (32.60 g, yield 100%) from a fraction eluted with ethyl acetate-hexane (1:3, v/v).

Workup

  1. stirringthe mixture was further stirred at room temperature for 15 hrs
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-8d7e0003e3b14fe5be7ea36ef6b14d1b
Source dataset
uspto-grants-2008_05
Patent number
US07368578B2

Reaction notes

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