Bis(3-hydroxyphenyl)ethane-1,2-dione → 1,2-Bis(3-hydroxyphenyl)ethanone

HRID 1414176Notes

Reaction equation

HRID 1414176 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([C:8]([C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([OH:18])[CH:13]=2)=O)=[O:9])[CH:5]=[CH:6][CH:7]=1>CN(C)C=O.O.C(OCC)(=O)C.[Zn]>[OH:1][C:2]1[CH:3]=[C:4]([C:8](=[O:9])[CH2:10][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([OH:18])[CH:13]=2)[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 1

HCID 13158606Bis(3-hydroxyphenyl)ethane-1,2-dione

Product 1

HCID 147741341,2-Bis(3-hydroxyphenyl)ethanoneYield 31.1%

Reagents, catalysts & solvents 4

HCID 23994ZincCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 3,3'-dihydroxybenzil (3.0 g.) and powdered zinc (5.0 g.) in N,N-dimethylformamide (25 ml.) and water (10 ml.) was stirred and heated under reflux for 6 hours. The cooled mixture was filtered through Celite and the filtrate was evaporated under oil pump vacuum to give a syrup. The syrup was dissolved in ethyl acetate and the solution was washed consecutively with dilute hydrochloric acid and saturated brine (thrice). The dried (MgSO4) solution was evaporated to smaller volume and benzene was added. A by-product (0.45 g., m.p. 225°-228°) crystallized on standing. The mother liquor was evaporated to a syrup which was crystallized by seeding from ethyl acetate benzene to give the title product (0.88 g., m.p. 151°-154°) which was shown to be identical with material produced from the two stage reduction (1, Sn/HCl; 2, Zn/chromic sulfate).

Workup

  1. temperatureheated
  2. temperatureunder reflux for 6 hours
  3. filtrationThe cooled mixture was filtered through Celite
  4. customthe filtrate was evaporated under oil pump vacuum
  5. customto give a syrup
  6. washthe solution was washed consecutively with dilute hydrochloric acid and saturated brine (thrice)
  7. dry with materialThe dried (MgSO4) solution
  8. customwas evaporated to smaller volume and benzene
  9. additionwas added
  10. customA by-product (0.45 g., m.p. 225°-228°) crystallized
  11. customThe mother liquor was evaporated to a syrup which
  12. customwas crystallized

Sources & evidence

ORD record
ord-207cc7d6a0bd4781a2dee3735e32833d
Source dataset
uspto-grants-1977_01
Patent number
US04001216

Reaction notes

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