tert-Butanol → 5-(9,12,15-Octadecatrien-1-yloxy)-2-furoic acid

HRID 1111419

反応式

HRID 1111419 の反応式
Br[C:2]1[O:6][C:5]([C:7]([OH:9])=[O:8])=[CH:4][CH:3]=1.[CH2:10]([OH:28])[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH:18]=[CH:19][CH2:20][CH:21]=[CH:22][CH2:23][CH:24]=[CH:25][CH2:26][CH3:27].CC(C)([O-])C.[K+].C(O)(C)(C)C>C1(C)C=CC=CC=1>[CH2:10]([O:28][C:2]1[O:6][C:5]([C:7]([OH:9])=[O:8])=[CH:4][CH:3]=1)[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH:18]=[CH:19][CH2:20][CH:21]=[CH:22][CH2:23][CH:24]=[CH:25][CH2:26][CH3:27]

参加物

6

反応物 4

HCID 6386tert-ButanolHCID 681699,12,15-Octadecatrien-1-olHCID 685115-Bromo-2-furanecarboxylic acidHCID 23665647Potassium tert-butoxide

生成物 1

HCID 543885795-(9,12,15-Octadecatrien-1-yloxy)-2-furoic acid

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

反応条件

温度
110 °C

実験手順

A mixture of 57.0 g (0.300 mole) of 5-bromo-2-furoic acid, 119.0 g (0.450 mole) of 9,12,15-octadecatrienol, and 84 g (0.750 mole) of potassium tert-butoxide in dry toluene is stirred with heating. The tert-butanol formed in the reaction is allowed to distill off, and the mixture is refluxed at 110° C. with stirring for 48 hours. The mixture is allowed to cool, then is acidified with acetic acid and diluted with ice-water. The toluene organic layer is separated, washed with water, then extracted three times with 5% sodium bicarbonate solution. The combined aqueous extracts are cooled and acidified with 10% HCl solution to give 5-(9,12,15-octadecatrien-1-yloxy)-2-furoic acid.

後処理

  1. temperaturewith heating
  2. distillationto distill off
  3. stirringwith stirring for 48 hours
  4. temperatureto cool
  5. additiondiluted with ice-water
  6. customThe toluene organic layer is separated
  7. washwashed with water
  8. extractionextracted three times with 5% sodium bicarbonate solution
  9. temperatureThe combined aqueous extracts are cooled

出典と根拠

ORDレコード
ord-0f579d1304014fe9b04ecd03eac60ec3
出典データセット
uspto-grants-1990_12
特許番号
US04980371

関連ノート

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