Furfural → 9-(2-Furyl)-8-nonenoic acid

HRID 1004472Notes

Reaction equation

HRID 1004472 reaction equation
[Br-].[C:2]([CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([OH:4])=[O:3].[O:31]1[CH:35]=[CH:34][CH:33]=[C:32]1[CH:36]=O>C1COCC1>[O:31]1[CH:35]=[CH:34][CH:33]=[C:32]1[CH:36]=[CH:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][C:2]([OH:4])=[O:3]

Participants

4

Reactant 2

HCID 7362FurfuralHCID 11317723(7-Carboxyheptyl)triphenylphosphonium bromide

Product 1

HCID 541079749-(2-Furyl)-8-nonenoic acidYield 61%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

This compound was synthesized from 7-carboxyheptyltriphenylphosphonium bromide (9.71 g, 20 mmol) and 2-furaldehyde (1.92 g, 20 mmol) in THF (100 mL) by a Wittig reaction. Kugelrohr distillation yielded the product (2.69 g, 61%) as a pale yellow oil (bp 136-139° C./0.05 torr). IR: 3500-2500, 1730, 710 cm-1 ; 1H-NMR: 1.40 (m, 8H), 2.35 (m, 4H), 5.55 (m, 1H), 6.30 (m, 3H), 7.35 (s, 1H), 11.40 (bs, 1H). Anal. Calcd. for C13H18O3 : C, 70.25, H. 8.16%; Found: C, 69.98, H, 8.26%. Z:E=79:21.

Workup

  1. distillationKugelrohr distillation

Sources & evidence

ORD record
ord-03e4f442ec7d43c7a2613dcbbc6538e9
Source dataset
uspto-grants-2000_04
Patent number
US06048989

Reaction notes

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