Dimethylformamide → HCID 17861251, compound

HRID 1294102Notes

Reaction equation

HRID 1294102 reaction equation
[CH2:1]([O:8][C:9]1[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][C:10]=1[CH:11]=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CN(C)C=O.[H-].[Na+].[CH3:25][O:26][CH2:27]Cl>O>[CH2:1]([O:8][C:9]1[CH:16]=[CH:15][C:14]([O:17][CH2:25][O:26][CH3:27])=[CH:13][C:10]=1[CH:11]=[O:12])[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 185361922-(Benzyloxy)-5-hydroxybenzaldehyde

Product 1

HCID 17861251HCID 17861251, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 2-benzyloxy-5-hydroxybenzaldehyde (16.68 g) and N,N-dimethylformamide (100 mL) was added sodium hydride (60%, oil, 3.07 g) under ice-cooling, and the mixture was stirred at room temperature for 30 min. Chloromethyl methyl ether (11.8 g) was dropwise added to the reaction mixture. The reaction mixture was further stirred at room temperature for 3 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-5-methoxymethoxybenzaldehyde as a colorless oil (10.32 g, 52%) from a fraction eluted with ethyl acetate-hexane (1:4, v/v).

Workup

  1. temperaturecooling
  2. stirringThe reaction mixture was further stirred at room temperature for 3 hrs
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-eb596bff777d4d67907752069d4bf65e
Source dataset
uspto-grants-2007_07
Patent number
US07238716B2

Reaction notes

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