Acetic Anhydride → PHENOL, 2,6-DIMETHYL-, ACETATE

HRID 345048Notes

Reaction equation

HRID 345048 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[OH:9].[C:10](OC(=O)C)(=[O:12])[CH3:11]>>[C:10]([O:9][C:3]1[C:4]([CH3:8])=[CH:5][CH:6]=[CH:7][C:2]=1[CH3:1])(=[O:12])[CH3:11]

Participants

3

Reactant 2

HCID 7918Acetic AnhydrideHCID 113352,6-Dimethylphenol

Product 1

HCID 101890PHENOL, 2,6-DIMETHYL-, ACETATEYield 102.5%

Procedure

100 g (0.82 mole) of 2,6-dimethylphenol and 167.4 g (1.64 mole) of acetic anhydride were refluxed for 4 h. The reaction mixture was poured onto ice and extracted with methylene chloride. The organic phase was washed with dilute sodium hydroxide solution, dried and concentrated under reduced pressure. 138 g of 2,6-dimethylphenyl acetate were obtained. To this product were added 120.2 g (0.9 mole) of anhydrous aluminum chloride in portions, during which the temperature rose to 85° C. The mixture was then heated at 110° C. for 30 min and left to cool. The viscous paste was poured onto ice/hydrochloric acid, and the precipitated product was filtered off. Recrystallization from 1/1 methanol/water resulted in 103.6 g of 3,5-dimethyl-4-hydroxyacetophenone.

Workup

  1. additionThe reaction mixture was poured onto ice
  2. extractionextracted with methylene chloride
  3. washThe organic phase was washed with dilute sodium hydroxide solution
  4. customdried
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-3d0300c868d94aa2a733f3a6c45f0a95
Source dataset
uspto-grants-1991_10
Patent number
US05055475

Reaction notes

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