Acetic Anhydride → 1-(2,4-Dihydroxy-3-methylphenyl)ethan-1-one

HRID 2425023Notes

Reaction equation

HRID 2425023 reaction equation
[CH3:1][C:2]1[C:7]([OH:8])=[CH:6][CH:5]=[CH:4][C:3]=1[OH:9].[C:10](OC(=O)C)(=[O:12])[CH3:11]>[Cl-].[Cl-].[Zn+2]>[OH:8][C:7]1[C:2]([CH3:1])=[C:3]([OH:9])[CH:4]=[CH:5][C:6]=1[C:10](=[O:12])[CH3:11]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 118432-Methylresorcinol

Product 1

HCID 5921391-(2,4-Dihydroxy-3-methylphenyl)ethan-1-one

Reagents, catalysts & solvents 1

HCID 3007855ZincchlorideCatalyst

Conditions

Temperature
105 °C

Procedure

A mixture of 2-methyl-benzene-1,3-diol, acetic anhydride and ZnCl2 was heated at 150-60° C. for 3.5 h, and processed as reported in the literature. (Pearson. D. E. et. al., Synthesis, 533, 1972 and the references cited therein). The crude was purified using flash chromatography (silica gel, 0-5% CH3CN in chloroform) to obtain the title compound. Yield, 73%; mp, 65-66° C. (EtOAc-PE 60-80° C.); MS (CI): 195 (M++29), 169 (M++1); analysis: C9H10O3 requires C, 65.05; H, 6.07. found C, 65.44; H, 6.62%.

Workup

  1. customet. al., Synthesis, 533, 1972
  2. customThe crude was purified

Sources & evidence

ORD record
ord-d0f440fd5499410682df4d94274dbc6b
Source dataset
uspto-grants-2011_06
Patent number
US07964628B2

Reaction notes

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