3-Hydroxyacetophenone → 1,2-Bis(3-hydroxyphenyl)ethanone

HRID 1414175Notes

Reaction equation

HRID 1414175 reaction equation
O[CH:2]([C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([OH:18])[CH:13]=1)[C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([OH:11])[CH:6]=1)=[O:4].OC1C=C(C(=O)C)C=CC=1.O.C(O)C>O.[Zn]>[OH:11][C:7]1[CH:6]=[C:5]([C:3](=[O:4])[CH2:2][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([OH:18])[CH:13]=2)[CH:10]=[CH:9][CH:8]=1

Participants

6

Reactant 3

HCID 84873-HydroxyacetophenoneHCID 19096565Water ethanolHCID 205128182-Hydroxy-1,2-bis(3-hydroxyphenyl)ethanone

Product 1

HCID 147741341,2-Bis(3-hydroxyphenyl)ethanone

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 962WaterSolvent

Procedure

2-Hydroxy-1,2-bis(3-hydroxyphenyl)ethanone was reduced by the procedure of M. Pisova and M. Soncek [Coll. Czech, Chem. Comm., 38, 3876 (1973)]. A mixture of 2-hydroxy-1,2-bis(3-hydroxyphenylethanone (18 g.) chromic sulfate hydrate (20.9% Cr; 60 g.), zinc dust (49 g.) and water-ethanol (1:1, 1 liter) was stirred under an atmosphere of nitrogen for 11 hours. The mixture was diluted with water and extracted with three portions of ethyl acetate. The organic solution was washed with saturated brine solution and dried over magnesium sulfate. The solution was concentrated and the product crystallized from ethyl acetate-benzene (seeding); yield: 8.51 g., m.p. 155°-156°.

Workup

  1. extractionextracted with three portions of ethyl acetate
  2. washThe organic solution was washed with saturated brine solution
  3. dry with materialdried over magnesium sulfate
  4. concentrationThe solution was concentrated
  5. customthe product crystallized from ethyl acetate-benzene (seeding)

Sources & evidence

ORD record
ord-80a53bf462214023a13715c5ef0a8bf5
Source dataset
uspto-grants-1977_01
Patent number
US04001216

Reaction notes

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