p-Toluenesulfonic acid monohydrate → 1-(2,4-Dihydroxyphenyl)-3-(4-hydroxyphenyl)prop-2-en-1-one

HRID 974370Notes

Reaction equation

HRID 974370 reaction equation
[OH:1][C:2]1[CH:24]=[C:23]([O:25]C2CCCCO2)[CH:22]=[CH:21][C:3]=1[C:4](=[O:20])[CH:5]=[CH:6][C:7]1[CH:12]=[CH:11][C:10]([O:13]C2CCCCO2)=[CH:9][CH:8]=1.C(Cl)Cl.CO.O.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>O>[OH:13][C:10]1[CH:11]=[CH:12][C:7]([CH:6]=[CH:5][C:4]([C:3]2[CH:21]=[CH:22][C:23]([OH:25])=[CH:24][C:2]=2[OH:1])=[O:20])=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 521998p-Toluenesulfonic acid monohydrateHCID 21958822Dichloromethane methanol waterHCID 54348409HCID 54348409, compound

Product 1

HCID 4251-(2,4-Dihydroxyphenyl)-3-(4-hydroxyphenyl)prop-2-en-1-oneYield 99.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 4,000 g of crude 2'-hydroxy-4,4'-bis(tetrahydropyranyloxy)chalcone (purity: 79.4%) and 13 ml of a mixed solvent of methylene chloride:methanol:water (4:4:1) was added 0.18 g of p-toluenesulfonic acid monohydrate, and the resulting mixture was agitated ar room temperature for 2 hours. The mixture was poured into 120 ml of water, and extracted with ethyl acetate. Distillation off of ethyl acetate afforded 2.770 g of 4,2',4'-trihydroxychalcone, having purity of 69.1% and yield of 99.9%.

Workup

  1. extractionextracted with ethyl acetate
  2. distillationDistillation off of ethyl acetate

Sources & evidence

ORD record
ord-9085b532173a420e992141386b4eed3a
Source dataset
uspto-grants-1991_11
Patent number
US05068364

Reaction notes

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