HCID 19744865, compound → Benzaldehyde, 4-(phenylmethoxy)-

HRID 2254276Notes

Reaction equation

HRID 2254276 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15](=[O:17])C)=[C:11](O)[C:10]=1CC=C(C)C)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>CS(C)=O>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([CH:15]=[O:17])=[CH:13][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 1

HCID 19744865HCID 19744865, compound

Product 1

HCID 78109Benzaldehyde, 4-(phenylmethoxy)-Yield 109.6%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

In 65 ml of dimethylsulfoxide were dissolved 20.01 g of the 4'-benzyloxy-2'-hydroxy-3'-(3-methyl-2butenyl)acetophenone obtained in Production Example 15 and 15.00 g of the 4-benzyloxybenzaldehyde obtained in Production Example 27, and 130 ml of a saturated ethanol solution of potassium hydroxide was added to the solution and the mixture was stirred at room temperature in a nitrogen current for 2.5 hours. After the reaction, the reaction liquid was diluted with water and was gradually made acidic by addition of 3 N hydrochloric acid under cooling. The formed precipitate was recovered by filtration and recrystallized from a mixed solvent of benzene and ethanol to obtain 23.64 g (yield=72.7%) of 4,4'-dibenzyloxy-2'-hydroxy-3+-(3-methyl-2-butenyl)chalcone in the form of a yellow needle.

Sources & evidence

ORD record
ord-efd9c471435a4ced8ee434b393987ccc
Source dataset
uspto-grants-1993_08
Patent number
US05234951

Reaction notes

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