Acetic Anhydride → HCID 18008627, compound

HRID 987371Notes

Reaction equation

HRID 987371 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15])[CH:5]=[CH:4][C:3]=1[OH:16].[C:17](OC(=O)C)(=[O:19])[CH3:18].[CH3:24]CCCCCC>S(=O)(=O)(O)O>[C:17]([O:16][C:3]1[CH:4]=[CH:5][C:6]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:24])=[CH:7][C:2]=1[CH3:1])(=[O:19])[CH3:18]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 8900HeptaneHCID 18008630HCID 18008630, compound

Product 1

HCID 18008627HCID 18008627, compoundYield 97.6%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidCatalyst

Procedure

4-Octyl-2-cresol (6a) (245.51 g, 1.116 mol) was treated with acetic anhydride (149.3 g, 1.45 mol) in the presence of a few drops of concentrated sulfuric acid at 110° C. for 1.5 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 (285.5 g) in 97.6% 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-5486f3d5ca404cc390ce585c09de4014
Source dataset
uspto-grants-2003_10
Patent number
US06632410B2

Reaction notes

Loading…