Acetic Acid → 3',4'-Dihydroxyacetophenone

HRID 1706693Notes

Reaction equation

HRID 1706693 reaction equation
C(O)(=O)C.Cl[CH2:6][C:7]([C:9]1[CH:10]=[C:11]([OH:16])[C:12](=[CH:14][CH:15]=1)[OH:13])=[O:8]>O.C(O)C.[Zn]>[C:7]([C:9]1[CH:10]=[C:11]([OH:16])[C:12](=[CH:14][CH:15]=1)[OH:13])(=[O:8])[CH3:6]

Participants

6

Reactant 2

HCID 176Acetic AcidHCID 668342-Chloro-3',4'-dihydroxyacetophenone

Product 1

HCID 145303',4'-Dihydroxyacetophenone

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

400 ml of a mixture of 1:8 v/v glacial acetic acid in water was added in two portions to a stirred mixture of 35 g of 4-(chloroacetyl)catechol in 300 ml of ethanol. At 10 minute intervals, four 10 g portions of 90% zinc dust were added, the mixture being held below about 45° C. The mixture then was stirred for 2 hours at 30°-40° C. and allowed to stand over a weekend. The liquid phase was decanted and stripped to a quarter of its volume under reduced pressure. The remaining mixture was extracted with ether, the extract was washed with sodium bicarbonate solution. The solvent was evaporated. The solid residue was recrystallized from toluene to give 4-acetylcatechol (9A), mp: 118°-119° C.

Workup

  1. custombeing held below about 45° C
  2. waitto stand over a weekend
  3. customThe liquid phase was decanted
  4. extractionThe remaining mixture was extracted with ether
  5. washthe extract was washed with sodium bicarbonate solution
  6. customThe solvent was evaporated
  7. customThe solid residue was recrystallized from toluene

Sources & evidence

ORD record
ord-e4435b7fcecc48b492c9c3c58d40eca8
Source dataset
uspto-grants-1980_06
Patent number
US04208424

Reaction notes

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