Water → [4-(3,4-Dichloro-benzyloxy)-phenyl]-oxo-acetaldehyde

HRID 391852

Reaction equation

HRID 391852 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:11])[CH:9]=[O:10])=[CH:4][CH:3]=1.[Cl:12][C:13]1[CH:14]=[C:15]([CH:18]=[CH:19][C:20]=1[Cl:21])[CH2:16]Br.C(=O)([O-])[O-].[K+].[K+].O>CN(C=O)C>[Cl:12][C:13]1[CH:14]=[C:15]([CH:18]=[CH:19][C:20]=1[Cl:21])[CH2:16][O:1][C:2]1[CH:3]=[CH:4][C:5]([C:8](=[O:11])[CH:9]=[O:10])=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 905684-HydroxyphenylglyoxalHCID 6397264-(Bromomethyl)-1,2-dichlorobenzene

Product 1

HCID 86654900[4-(3,4-Dichloro-benzyloxy)-phenyl]-oxo-acetaldehydeYield 84.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of (4-hydroxy-phenyl)-oxo-acetaldehyde (756 mg) in dry DMF (10 mL) were added 3,4-dichlorobenzylbromide (1.2 g) and potassium carbonate (1.03 g). After 4 hours, the reaction mixture was poured into water (100 mL) and extracted with ethyl acetate (2×50 mL). The organic extracts were then combined and washed with brine (2×50 mL) and a saturated sodium bicarbonate solution (2×50 mL). The organic layer was dried over sodium sulfate and concentrated under reduced pressure to give [4-(3,4-dichloro-benzyloxy)-phenyl]-oxo-acetaldehyde (1.3 g).

Workup

  1. extractionextracted with ethyl acetate (2×50 mL)
  2. washwashed with brine (2×50 mL)
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-190e1298460940999e520fe963dbd425
Source dataset
uspto-grants-2013_02
Patent number
US08383644B2

Linked notes

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