Butyl vinyl ether → HCID 54018124, compound

HRID 1576132Notes

Reaction equation

HRID 1576132 reaction equation
[CH3:1][C:2](O)([CH2:4][CH2:5][CH2:6][C:7]([CH:9]=[CH2:10])=[CH2:8])[CH3:3].[CH:12]([O:14]CCCC)=[CH2:13].C([O-])(=O)C.[Na+]>>[CH3:1][C:2](=[CH:4][CH2:5][CH2:6][C:7]([CH:9]=[CH2:10])=[CH2:8])[CH2:3][CH2:13][CH:12]=[O:14]

Participants

4

Reactant 3

HCID 8108Butyl vinyl etherHCID 109752-Methyl-6-methylene-7-octen-2-olHCID 517045Sodium Acetate

Product 1

HCID 54018124HCID 54018124, compoundYield 75%

Procedure

A mixture of 50 g. of sec.-myrcenol (prepared according to the method described in paragraph b) above), 300 g. of n-butyl vinyl ether, 1 g. of mercuric acetate and 10 g. of sodium acetate were refluxed for 40 hours (120°) under nitrogen. During this heating period 1 g. of additional mercuric acetate was added every 6 hours. The laboratory vessel was connected to a downward directed condenser, and the excess of n-butyl vinyl ether was distilled under ordinary pressure. The residue was distilled under vacuum. A yield of 75% of 4-methyl-8-vinyl-4,8-nonadienal that contained approximately 15% of unreacted alcohol was obtained. This alcohol could be recovered when the above C12 aldehyde was converted to β-sinensal.

Workup

  1. additionA mixture of 50 g
  2. waitDuring this heating period 1 g
  3. distillationthe excess of n-butyl vinyl ether was distilled under ordinary pressure
  4. distillationThe residue was distilled under vacuum

Sources & evidence

ORD record
ord-955e40a26c0041719938eacd1ac0ce36
Source dataset
uspto-grants-1976_09
Patent number
US03979425

Reaction notes

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