Furfural → 11-(2-Furyl)-10-undecenoic acid

HRID 377492ノート

反応式

HRID 377492 の反応式
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH:6]=O.[Br-].[C:9]([CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([OH:11])=[O:10]>C1COCC1>[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH:6]=[CH:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][C:9]([OH:11])=[O:10]

参加物

4

反応物 2

HCID 7362FurfuralHCID 18795071(9-Carboxynonyl)(triphenyl)phosphanium bromide

生成物 1

HCID 5443923211-(2-Furyl)-10-undecenoic acid収率 59%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

This compound was synthesized from 2-furaldehyde (1.92 g, 20 mmol) and 9-carboxynonyltriphenylphosphonium bromide (10.27 g, 20 mmol) in THF (100 mL) by a Wittig reaction. Crystallization (petroleum ether) afforded the product (2.95 g, 59%) as white crystals (mp 45-46° C.); IR: 3450-2500 cm-1 ; 1H-NMR: 1.33 (m, 8H), 1.46 (m, 2H), 1.65 (m, 2H), 2.34 (t, 2H), 2.45 (m, 2H), 5.55 (m, 1H), 6.18 (d, 1H), 6.25 (d, 1H), 6.38 (d, 1H), 7.38 (s, 1H), 9.80 (bs, 1H). Anal. Calcd. for C15H22O3 :C, 71.97, H, 8.86%; Found: C, 71.93, H, 8.87%. Z:E=43:57.

後処理

  1. customCrystallization (petroleum ether)

出典と根拠

ORDレコード
ord-3112a83a50f0401aa8dc198a03d1bc90
出典データセット
uspto-grants-2000_02
特許番号
US06025511

反応ノート

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