Reaction #11287

ord-b29dfb38e38e4655b60cb3c4a305e099

Reaction equation

CC(C)=CCCC(C)=CC(C)O
4,8-dimethyl-3,7-nonadien-2-ol
c1ccncc1
pyridine
O
water
→
CCCC(=O)OC(C)C=C(C)CCC=C(C)C
crude product
Yield 76.0%
CCCC(=O)OC(C)C=C(C)CCC=C(C)C
4,8-Dimethyl-3,7-nonadien-2-yl Butyrate
Yield 76.0%

Reactants

—
anhydride
CC(C)=CCCC(C)=CC(C)O
4,8-dimethyl-3,7-nonadien-2-ol
c1ccncc1
pyridine
O
water

Reagents

None

Solvents

COC(C)(C)C
methyl t-butyl ether

Conditions

Temperature
100°CELSIUS
Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    Temperaturecooled to room temperature
  2. 2
    Washwashed several times with water until neutral pH
  3. 3
    Dryingdried over sodium sulfate
  4. 4
    Concentrationconcentrated

Procedure

A flask was charged with 4,8-dimethyl-3,7-nonadien-2-ol CAS 67845-50-5 (20 grams), buryric anhydride (25 grams) and pyridine (12.5 grams). The mixture was stirred and heated to 100° C. The reaction was held at 100° C.±1° C. for 90 minutes and then cooled to room temperature. The reaction mixture was diluted with water (100 milliliters) and methyl t-butyl ether, washed several times with water until neutral pH, dried over sodium sulfate and concentrated to furnish 34.4 grams of crude product. After distillation by Kugelruhr 23.4 g of the product, 76% yield, were obtained and confirmed by 1H NMR.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07097872B2uspto-grants-2006_08