Hydrofluoric Acid → trans Ethyl 11-fluoro-3,7,11-trimethyldodeca-2,4-dienoate

HRID 918311Notes

Reaction equation

HRID 918311 reaction equation
[CH3:1][C:2](/[CH:9]=[CH:10]/[CH2:11][CH:12]([CH3:19])[CH2:13][CH2:14][CH:15]=[C:16]([CH3:18])[CH3:17])=[CH:3][C:4]([O:6][CH2:7][CH3:8])=[O:5].[FH:20]>O1CCCC1>[F:20][C:16]([CH3:17])([CH3:18])[CH2:15][CH2:14][CH2:13][CH:12]([CH3:19])[CH2:11]/[CH:10]=[CH:9]/[C:2]([CH3:1])=[CH:3][C:4]([O:6][CH2:7][CH3:8])=[O:5]

Participants

4

Reactant 2

HCID 14917Hydrofluoric AcidHCID 86733725trans Ethyl 3,7,11-trimethyldodeca-2,4,10-trienoate

Product 1

HCID 86733724trans Ethyl 11-fluoro-3,7,11-trimethyldodeca-2,4-dienoate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

One gram of trans ethyl 3,7,11-trimethyldodeca-2,4,10-trienoate is added to a solution of 1 equiv. of dry hydrogenfluoride in dry tetrahydrofuran. The mixture is allowed to stand at 0° for 15 hours and is then washed with water, dried and evaporated under reduced pressure to yield trans ethyl 11-fluoro-3,7,11-trimethyldodeca-2,4-dienoate which can be purified by chromatography.

Workup

  1. washis then washed with water
  2. customdried
  3. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-41a26b0ed936409280a4b03ab534de36
Source dataset
uspto-grants-1976_07
Patent number
US03970704

Reaction notes

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