Methanol → 1-(2,4-Dihydroxyphenyl)-3-(4-Hydroxyphenyl)Prop-2-En-1-One

HRID 974368Notes

Reaction equation

HRID 974368 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.C1(C)C=CC(S(O)(=O)=O)=CC=1.CO>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 887MethanolHCID 6101p-Toluenesulfonic acidHCID 54348409HCID 54348409, compound

Product 1

HCID 4251-(2,4-Dihydroxyphenyl)-3-(4-Hydroxyphenyl)Prop-2-En-1-OneYield 77.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 4,000 g of crude 2'-hydroxy-4,4'-bis(tetrahydropyranyloxy)chalcone (purity: 79.4%), 64 mg of p-toluenesulfonic acid and 12 ml of methanol was agitated at room temperature for 2 hours. The mixture was poured into 120 ml of water, and crystals which formed were filtered and washed with 250 ml of water. The crystals obtained were dried to obtain 1.836 g of 4,2',4'-trihydroxychalcone having purity of 79.4% and yield of 77.4%.

Workup

  1. customformed
  2. filtrationwere filtered
  3. washwashed with 250 ml of water
  4. customThe crystals obtained
  5. customwere dried

Sources & evidence

ORD record
ord-ba61ad7c0d274f78ae3431135c582168
Source dataset
uspto-grants-1991_11
Patent number
US05068364

Reaction notes

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