Acetic Anhydride → 2-methyl-3-cyclohexylpropyl Acetate

HRID 635156Notes

Reaction equation

HRID 635156 reaction equation
[CH3:1][CH:2]([CH2:5][CH:6]1[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1)[CH2:3][OH:4].CN(C1C=CC=CN=1)C.C(N(CC)CC)C.[C:28](OC(=O)C)(=[O:30])[CH3:29]>C1(C)C=CC=CC=1>[C:28]([O:4][CH2:3][CH:2]([CH3:1])[CH2:5][CH:6]1[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1)(=[O:30])[CH3:29]

Participants

6

Reactant 4

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 218852-DimethylaminopyridineHCID 107970123-Cyclohexyl-2-methylpropan-1-ol

Product 1

HCID 155111252-methyl-3-cyclohexylpropyl AcetateYield 98%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
0 °C

Procedure

To a cooled (0° C.), stirred solution of 2-methyl-3-cyclohexylpropanol (40.3 g., 0.26 mol.), dimethylaminopyridine (2.5 g., 0.02 mol.), and triethylamine (38.4 g., 0.38 mol.) in 200 ml of toluene was added acetic anhydride (39.4 g. 0.39 mol) over 30 minutes. The resulting solution was allowed to warm to room temperature and stirred for an additional 1.5 hours. The reaction mixture was washed twice with 125 ml portions of 2 N aqueous sodium chloride, dried over magnesium sulfate and concentrated to a colorless oil which was distilled to obtain 72 g. 98% yield; bp 67-71° C. at 0.6 mm. Odor: very pleasant fruity, rosy, floral. Mass Spectrum from 5508-36. MS (El) m/z (relative intensity) 155 (M+−C2H3O, 2), 138 (M+−C2H4O2, 15).

Workup

  1. temperatureto warm to room temperature
  2. washThe reaction mixture was washed twice with 125 ml portions of 2 N aqueous sodium chloride
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated to a colorless oil which
  5. distillationwas distilled
  6. customto obtain 72 g

Sources & evidence

ORD record
ord-42f49c844c874c6cb628615b4a10b3ab
Source dataset
uspto-grants-2001_02
Patent number
US06187727B1

Reaction notes

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