Dimethylformamide → HCID 14972990, compound

HRID 845767Notes

Reaction equation

HRID 845767 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH2:7]Cl)=[CH:5][CH:4]=1.[H-].[Na+].CN(C)[CH:15]=[O:16]>>[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH2:7][O:2][C:3]2[CH:4]=[C:5]([CH:6]=[CH:9][CH:10]=2)[CH:15]=[O:16])=[CH:5][CH:4]=1

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 699934-Methyloxybenzyl chloride

Product 1

HCID 14972990HCID 14972990, compound

Procedure

m-Hydroxybenzaldehyde (24.1 g., 0.197 mole) was dissolved in 150 ml. of dimethylformamide. To this solution were added p-methoxybenzyl chloride (9.5 g., 0.197 mole) and 50% sodium hydride (in mineral oil) in small portions at room temperature. The reaction was stirred under an argon atmosphere for 2 hours, then allowed to stand overnight. The reaction mixture was poured into a large volume of ice water. The product 3-(p-methoxybenzyloxy)benzaldehyde was collected and recrystallized from ethanol; 42.9 g., mp 78° C.

Workup

  1. dissolutionm-Hydroxybenzaldehyde (24.1 g., 0.197 mole) was dissolved in 150 ml
  2. waitto stand overnight
  3. customThe product 3-(p-methoxybenzyloxy)benzaldehyde was collected
  4. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-76598a10559344ada9eef16436cfa005
Source dataset
uspto-grants-1988_07
Patent number
US04760089

Reaction notes

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