Benzaldehyde → Nonanal, 2-(phenylmethylene)-

HRID 463995

Reaction equation

HRID 463995 reaction equation
[CH2:1]([C:8](=[CH:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH:9]=[O:10])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7].C(=O)C1C=CC=CC=1.[OH-].[Na+].C(=O)CCCCCCCC>>[CH2:11]([CH:8]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7])[CH2:9][OH:10])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[CH2:1]([C:8](=[CH:11][C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)[CH:9]=[O:10])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7]

Participants

6

Reactant 4

HCID 240BenzaldehydeHCID 14798Sodium Hydroxide2×HCID 31289Nonanal2×HCID 89284Nonanal, 2-(phenylmethylene)-

Product 2

HCID 89284Nonanal, 2-(phenylmethylene)-HCID 202634712-Benzyl-1-nonanol

Procedure

The alcohol was prepared by hydrogenation of a-heptylcinnamaldehyde exactly as in Example 1. -Heptylcinnamaldehyde was prepared as follows: To a mixture of 53.8 g (0.50 mole) benzaldehyde 50 ml ethanol and 25 ml 10% NaOH at reflux were added 56.8 g (0.40 mole) nonanal dropwise over 20 min. Halfway through the addition of nonanal an additional 25 ml 10% NaOH were added. After two hours at reflux the mixture was cooled, diluted with 100 ml 30°-60° petroleum ether, washed once with 50 ml 5% HCl, once with saturated NaCl brine, filtered through 4A molecular sieves, stripped and fractionally distilled, bp 135°-150°/0.15 mm, to give 56.1 g (61%) whose IR showed aromatic CH stretch from 3000-3100 cm-1, aldehyde CH at 2705 cm-1, and an aldehyde C=0 at 1706 cm-1.

Workup

  1. temperatureat reflux
  2. additionwere added
  3. temperatureAfter two hours at reflux the mixture
  4. temperaturewas cooled
  5. washwashed once with 50 ml 5% HCl, once with saturated NaCl brine
  6. filtrationfiltered through 4A molecular sieves
  7. distillationfractionally distilled
  8. custombp 135°-150°/0.15 mm, to give 56.1 g (61%) whose IR

Sources & evidence

ORD record
ord-eb279c66bb34401daf98b1bfc76bbacb
Source dataset
uspto-grants-1985_10
Patent number
US04545912

Linked notes

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