Propionic Acid → HCID 10987849, compound

HRID 2058132Notes

Reaction equation

HRID 2058132 reaction equation
[CH3:1][C:2]([CH:4](O)[CH2:5][CH2:6][C:7](=[CH2:10])[CH:8]=[CH2:9])=[CH2:3].[C:12](OCC)([O:17]CC)([O:14][CH2:15][CH3:16])[CH3:13].C(O)(=O)CC>N1C=CC=CC=1>[CH3:1]/[C:2](=[CH:4]\[CH2:5][CH2:6][C:7](=[CH2:10])[CH:8]=[CH2:9])/[CH2:3][CH2:13][C:12]([O:14][CH2:15][CH3:16])=[O:17]

Participants

5

Reactant 3

HCID 1032Propionic AcidHCID 66221Triethyl orthoacetateHCID 534462HCID 534462, compound

Product 1

HCID 10987849HCID 10987849, compoundYield 70.5%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
135 °C

Procedure

A mixture of 2-methyl-6-methylene-1,7-octadien-3-ol (34 g, 0.224 M), triethyl orthoacetate (80 g, 0.5 M) and propionic acid (1 ml) is heated at 135° C. (bath temperature) under nitrogen for four hours. The resulting mixture is cooled to room temperature and treated with pyridine (1 ml). Most of the excess reagent is removed in vacuo (high vacuum pump) and the residue is purified by column chromatography on silica gel (300 g) with 5% ether in petroleum ether, to give ethyl 4-methyl-8-methylene-(E)-4,9-decadienoate (35 g, 70%) as a colorless liquid.

Workup

  1. temperatureThe resulting mixture is cooled to room temperature
  2. customMost of the excess reagent is removed in vacuo (high vacuum pump)
  3. customthe residue is purified by column chromatography on silica gel (300 g) with 5% ether in petroleum ether

Sources & evidence

ORD record
ord-0e476b4a9cfa47efa0db138f1cc69446
Source dataset
uspto-grants-1980_07
Patent number
US04215048

Reaction notes

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