Potassium Carbonate → 4-(2-Chlorobenzyloxy)-3,5-dichlorophenoxyacetaldehyde diethyl acetal

HRID 363100Notes

Reaction equation

[Cl:1][C:2]1[CH:18]=[CH:17][CH:16]=[CH:15][C:3]=1[CH2:4][O:5][C:6]1[C:11]([Cl:12])=[CH:10][C:9]([OH:13])=[CH:8][C:7]=1[Cl:14].[CH2:19]([O:21][CH:22]([O:25][CH2:26][CH3:27])[CH2:23]Br)[CH3:20].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH2:19]([O:21][CH:22]([O:25][CH2:26][CH3:27])[CH2:23][O:13][C:9]1[CH:10]=[C:11]([Cl:12])[C:6]([O:5][CH2:4][C:3]2[CH:15]=[CH:16][CH:17]=[CH:18][C:2]=2[Cl:1])=[C:7]([Cl:14])[CH:8]=1)[CH3:20]

Participants

Conditions

Temperature: 90 °C

Procedure

A mixture of 0.85 g of 4-(2-chlorobenzyloxy)-3,5-dichlorophenol, 0.47 ml of bromoacetaldehyde diethyl acetal, 0.46 g of potassium carbonate and 20 ml of N,N-dimethylformamide was stirred at 90° C. for 6 hours. After cooling to room temperature, the reaction mixture was poured into ice water, and extracted twice with 50 ml of diethyl ether. The combined ether layer was washed with water, and dried with anhydrous magnesium sulfate, followed by removal of the solvent by distillation under reduced pressure. The residue was subjected to silica gel chromatography, which afforded 0.85 g of 4-(2-chlorobenzyloxy)-3,5-dichlorophenoxyacetaldehyde diethyl acetal (72% yield).

Workup

temperatureAfter cooling to room temperature
extractionextracted twice with 50 ml of diethyl ether
washThe combined ether layer was washed with water
dry with materialdried with anhydrous magnesium sulfate
customfollowed by removal of the solvent by distillation under reduced pressure

Sources & evidence

ORD record: ord-6300e521e43f44889713381f2ba869df
Source dataset: uspto-grants-1999_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05872137

Reaction notes

Loading…