Acetic Anhydride → HCID 18008627, compound

HRID 987363Notes

Reaction equation

HRID 987363 reaction equation
[CH2:1]([C:10]1[CH:11]=[C:12]([CH3:17])[C:13]([OH:16])=[CH:14][CH:15]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9].[C:18](OC(=O)C)(=[O:20])[CH3:19]>S(=O)(=O)(O)O.CCCCCCC>[C:18]([O:16][C:13]1[CH:14]=[CH:15][C:10]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9])=[CH:11][C:12]=1[CH3:17])(=[O:20])[CH3:19]

Participants

5

Reactant 2

HCID 7918Acetic AnhydrideHCID 844264-Nonyl-o-cresol

Product 1

HCID 18008627HCID 18008627, compoundYield 99.7%

Reagents, catalysts & solvents 2

HCID 1118Sulfuric AcidCatalystHCID 8900HeptaneSolvent

Procedure

4-Nonyl-2-cresol (1a) (934 g, 3.99 mol) was treated with acetic anhydride (456.6 g, 4.42 mol) in the presence of a few drops of concentrated sulfuric acid at 110° C. for 1 h. After cooling to ambient temperature, the reaction mixture was transferred into a 4-I separatory funnel with aid of heptane (400 mL). The resulting organic phase was washed with aqueous sodium bicarbonate solution and water until the pH became 6 or so. The heptane phase was dried over sodium sulfate and concentrated to obtain 4-nonyl-2-methylphenyl acetate (1098.3 g) in 99.7% yield.

Workup

  1. washThe resulting organic phase was washed with aqueous sodium bicarbonate solution and water until the pH
  2. dry with materialThe heptane phase was dried over sodium sulfate
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-4050630942684756af4ab709131dd95b
Source dataset
uspto-grants-2003_10
Patent number
US06632410B2

Reaction notes

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