Propionic Acid → Ethyl 5,9,13-trimethyl-3,4,8,12-pentadecatetraenoate

HRID 1284166Notes

Reaction equation

HRID 1284166 reaction equation
[C:1]([O-:7])([O-])([O:3][CH2:4][CH3:5])[CH3:2].[CH3:8][C:9]([CH3:23])=[CH:10][CH2:11][CH2:12]/[C:13](/[CH3:22])=[CH:14]/[CH2:15][CH2:16][C:17](O)([C:19]#[CH:20])[CH3:18].[C:24](O)(=O)CC>>[CH3:8][C:9]([CH2:10][CH2:11][CH:12]=[C:13]([CH3:22])[CH2:14][CH2:15][CH:16]=[C:17]([CH3:18])[CH2:19][CH3:20])=[C:23]=[CH:24][CH2:2][C:1]([O:3][CH2:4][CH3:5])=[O:7]

Participants

4

Reactant 3

HCID 1032Propionic AcidHCID 53658233,7,11-Trimethyldodeca-6,10-dien-1-yn-3-olHCID 86598186Ethyl ortho-acetate

Product 1

HCID 53828293Ethyl 5,9,13-trimethyl-3,4,8,12-pentadecatetraenoateYield 96%

Procedure

In the same manner as in the preceeding Examples, 32.4 g of ethyl ortho-acetate, 22 g of dehydronerolidol and 1.5 g of propionic acid were reacted at 135 to 140°C. for 6 hours and the resulting reaction mixture was subjected to distillation under reduced pressure. Ethyl 5,9,13-trimethyl-3,4,8,12-pentadecatetraenoate was obtained in a yield of 96% from a fraction boiling at 144 to 146°C. under 0.025 mm Hg.

Workup

  1. customwere reacted at 135 to 140°C. for 6 hours
  2. customthe resulting reaction mixture
  3. distillationwas subjected to distillation under reduced pressure

Sources & evidence

ORD record
ord-1210a4fe341b4cc0a4c105b66796067c
Source dataset
uspto-grants-1976_08
Patent number
US03978100

Reaction notes

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