Furfural → 12-(2-Furyl)-11-dodecenoic acid

HRID 962985Notes

Reaction equation

HRID 962985 reaction equation
[Br-].[C:2]([CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([OH:4])=[O:3].[CH:34](=O)[C:35]1[O:39][CH:38]=[CH:37][CH:36]=1>C1COCC1>[O:39]1[CH:38]=[CH:37][CH:36]=[C:35]1[CH:34]=[CH:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][C:2]([OH:4])=[O:3]

Participants

4

Reactant 2

HCID 7362FurfuralHCID 11432504Phosphonium, (10-carboxydecyl)triphenyl-, bromide

Product 1

HCID 5422869012-(2-Furyl)-11-dodecenoic acidYield 45%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

This compound was synthesized from 10-carboxydecyltriphenylphosphonium bromide (10.50 g, 20 mmol) and furfural (1.92 g, 20 mmol) in THF (100 mL) by a Wittig reaction. Crystallization afforded the product (2.38 g, 45%) as pale yellow crystals (mp 38°-39° C.); IR: 3450-2500, 1715, 695 cm-1 ; 1H-NMR: 1.35 (m, 14H), 2.35 (t, 4H), 5.60 (m, 1H), 6.30 (m, 3H), 7.35 (s, 1H), 9.40 (bs, 1H). Anal. Calcd. for C16 H24O3 : C, 72.69, H, 9.15; Found: C, 72.44, H, 9.06%. Z:E=43:57.

Workup

  1. customCrystallization

Sources & evidence

ORD record
ord-c6a99612c53a4846a6ddafde9e6fe485
Source dataset
uspto-grants-1998_06
Patent number
US05760259

Reaction notes

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