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

HRID 326667Notes

Reaction equation

HRID 326667 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-5029a618ccc54bf0a00869f8356901b1
Source dataset
uspto-grants-1993_12
Patent number
US05270325

Reaction notes

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