Acetic Anhydride → HCID 53721729, compound

Reaction equation

[CH2:1]=[CH:2][CH2:3][CH:4]([OH:12])[CH:5]=[CH:6][CH2:7][CH2:8][CH2:9]CC.[C:13](OC(=O)C)(=[O:15])[CH3:14]>>[C:13]([O:12][CH:4]([CH:5]=[CH:6][CH2:7][CH2:8][CH3:9])[CH2:3][CH:2]=[CH2:1])(=[O:15])[CH3:14]

Participants

Reactant 2

HCID 7918Acetic Anhydride

HCID 30175341,5-Undecadien-4-ol

Product 1

HCID 53721729HCID 53721729, compoundYield 75%

Procedure

36 g of 1,5-undecadien-4-ol is stirred and heated to reflux with 32.6 g of acetic acid anhydride for 1 hour. The excess anhydride and the resulting acetic acid are removed by distillation under reduced pressure. The residue is fractionated. Yield: 33.8 g (76%) 1,5-undecadien-4-yl acetate; b.p. 70°-80° C/2 Torr; n20D = 1.4468. 1,5-Nonadien-4-yl acetate was prepared in a similar way; yield: 75%; b.p. 85° C/10 Torr; n22D = 1.4403.

Workup

temperatureheated
customThe excess anhydride and the resulting acetic acid are removed by distillation under reduced pressure

Sources & evidence

ORD record: ord-f1f2e628b7c049ba8349cf0fd2461f90
Source dataset: uspto-grants-1978_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04104202

Reaction notes

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