4-Propylbenzaldehyde → 8-(p-Propylphenyl)-7-octenenitrile

HRID 377481

Reaction equation

HRID 377481 reaction equation
[Br-].[C:2]([CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)#[N:3].[CH2:29]([C:32]1[CH:39]=[CH:38][C:35]([CH:36]=O)=[CH:34][CH:33]=1)[CH2:30][CH3:31]>C1COCC1>[CH2:29]([C:32]1[CH:39]=[CH:38][C:35]([CH:36]=[CH:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][C:2]#[N:3])=[CH:34][CH:33]=1)[CH2:30][CH3:31]

Participants

4

Reactant 2

HCID 1200474-PropylbenzaldehydeHCID 187950896-Cyanohexyltriphenylphosphonium bromide

Product 1

HCID 538329298-(p-Propylphenyl)-7-octenenitrileYield 67.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

This compound was synthesized from 6-cyanohexyltriphenylphosphonium bromide (9.05 g, 20 mmol) and p-propylbenzaldehyde (2.96 g, 20 mmol) in THF (100 mL) by a Wittig reaction. Kugelrohr distillation afforded the product (3.25 g, 67%) as a colorless liquid (bp 144-148° C./0.05 torr). IR 2290 cm-1 ; 1H-NMR: 0.95 (t, 3H), 1.55 (m, 8H), 2.40 (m, 6H), 5.60 (in, 1H), 6.40 (d, 1H), 7.10 (s, 4H).

Workup

  1. distillationKugelrohr distillation

Sources & evidence

ORD record
ord-e99ba9b7cc9145569e022762e357c18c
Source dataset
uspto-grants-2000_02
Patent number
US06025511

Linked notes

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