Hydrochloric Acid → 6-hydroxy-2-(4-methoxyphenyl)chroman-4-one

HRID 2108052Notes

Reaction equation

HRID 2108052 reaction equation
Cl.[CH3:2][C:3]([C:5]1[CH:10]=[C:9]([OH:11])[CH:8]=[CH:7][C:6]=1[OH:12])=[O:4].[CH3:13][O:14][C:15]1[CH:16]=[CH:17][C:18]([CH:21]=[O:22])=[CH:19][CH:20]=1>C(O)C>[OH:11][C:9]1[CH:10]=[C:5]2[C:6](=[CH:7][CH:8]=1)[O:12][CH:21]([C:18]1[CH:17]=[CH:16][C:15]([O:14][CH3:13])=[CH:20][CH:19]=1)[CH2:2][C:3]2=[O:4].[OH:12][C:6]1[CH:7]=[CH:8][C:9]([OH:11])=[CH:10][C:5]=1[CH:3]=[CH:2][C:21]([C:18]1[CH:17]=[CH:16][C:15]([O:14][CH3:13])=[CH:20][CH:19]=1)=[O:22]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 102792-AcetylhydroquinoneHCID 312444-Methoxybenzaldehyde

Product 2

HCID 118180796-hydroxy-2-(4-methoxyphenyl)chroman-4-oneHCID 70356590HCID 70356590, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

HCl is passed for 4 hours, with stirring, into a solution of 15.2 g of 2,5-dihydroxyacetophenone and 27.2 g of anisaldehyde in 1,500 ml of ethanol. 3-p-Methoxybenzylidene-6-hydroxy-4'-methoxyflavanone is precipitated, m.p. 199°-201°. 6-Hydroxy-4'-methoxyflavanone and 2,5-dihydroxy-p-methoxybenzylideneacetophenone are formed as intermediates.

Workup

  1. custom3-p-Methoxybenzylidene-6-hydroxy-4'-methoxyflavanone is precipitated

Sources & evidence

ORD record
ord-e1e52db5d9484b699d1ca26b9f24b275
Source dataset
uspto-grants-1990_06
Patent number
US04937257

Reaction notes

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