Ethyl Acetate → HCID 19886052, compound

HRID 655048Notes

Reaction equation

HRID 655048 reaction equation
[OH:1][C:2]1[C:9]([OH:10])=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].C(=O)([O-])[O-].[K+].[K+].[CH3:17][O:18][C:19]1[CH:26]=[CH:25][C:22]([CH2:23]Br)=[CH:21][CH:20]=1.[C:27]([O:30][CH2:31][CH3:32])(=O)C>CN(C)C=O.O>[CH3:17][O:18][C:19]1[CH:26]=[CH:25][C:22]([CH2:23][O:1][C:2]2[C:9]([O:10][CH2:6][C:3]3[CH:4]=[CH:32][C:31]([O:30][CH3:27])=[CH:9][CH:2]=3)=[CH:8][CH:7]=[CH:6][C:3]=2[CH:4]=[O:5])=[CH:21][CH:20]=1

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 905792,3-DihydroxybenzaldehydeHCID 1650214-Methoxybenzyl bromide

Product 1

HCID 19886052HCID 19886052, compoundYield 87%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 2,3-dihydroxybenzaldehyde (1) (6.91 g; 50 mMol.) in N, N-dimethylformamide (70 ml) cooling at 0° C. are added potassium carbonate power (17.97 g; 2.6 Eq.) and p-methoxybenzyl bromide (26.14 g; 2.6 Eq.), and the mixture is stirred at room temperature for 4 hours. ##STR12## The reaction mixture is dilued with ethyl acetate and water. The organic layer is washed with water, dried, and concentrated under reduced pressure. The residue is crystallized from a mixture of ether and hexane to give 2,3-di(p-methoxybenzyloxy)benzaldehyde (2) (16.43 g).

Workup

  1. washThe organic layer is washed with water
  2. customdried
  3. concentrationconcentrated under reduced pressure
  4. customThe residue is crystallized from a mixture of ether and hexane

Sources & evidence

ORD record
ord-2cd70ad4deaa4914a82fe6da3fab230a
Source dataset
uspto-grants-1992_07
Patent number
US05134138

Reaction notes

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