2-Phenylethanol → Phenethyl valerate

HRID 506415

반응식

HRID 506415 반응식
[C:1]([OH:7])(=[O:6])[CH2:2][CH2:3][CH2:4][CH3:5].[C:8]1([CH2:14][CH2:15]O)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>C([O-])(=O)C([O-])=O.[Sn+4].C([O-])(=O)C([O-])=O>[C:1]([O:7][CH2:15][CH2:14][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)(=[O:6])[CH2:2][CH2:3][CH2:4][CH3:5]

참가 물질

4

반응물 2

HCID 60542-PhenylethanolHCID 7991Pentanoic Acid

생성물 1

HCID 81964Phenethyl valerate수율 74.7%

시약·촉매·용매 1

HCID 9839089Oxalate;tin(4+)촉매

반응 조건

온도
170 °C

실험 절차

A 2-L, 4-neck, round-bottom flask, fitted with a thermometer, mechanical stirrer, nitrogen inlet tube and Liebig condenser/receiving flask, was charged with 612.8 g (6.00 mol, 1.00 equiv) of pentanoic acid, 733.0 g (6.00 mol, 1.00 equiv) of 2-phenylethanol, and 2.50 g (0.2 wt. %) of tin oxalate (Fascat® 2001). The air was removed with three cycles of evacuation/nitrogen-fill using a mechanical vacuum pump (50-100 torr). The rate of stirring was set at ca. 200 rpm, the nitrogen sparge was set at 0.1 scfh, and the reaction mixture was heated to 170° C. After a 1-h hold, 159.3 g of distillate had been collected. It was not possible to get a clean separation; therefore, the organic layer was not returned to the reaction mixture. The temperature was increased to 180, 190, 200 and 210° C. and held for 1 h at each; the amounts of distillate were 21.4, 9.8, 4.9 and 2.2 g, respectively. The acid number was 2.88 mg KOH/g (99.0% conversion). The excess 2-phenylethanol (6.3% by GLC) was removed by vacuum distillation through a 15-cm Vigreux column at 140-165° C. (15-20 torr). The crude product was distilled at 150-155° C. (10 torr, 0.5 scfh nitrogen sweep) to afford 925 g (75%) of 2-phenylethyl pentanoate (99.3% pure by GLC): residual alcohol, 0.3% (GLC); APHA color, 13; acid number, 0.06 mg KOH/g; saponification number, 271 mg KOH/g (theor. 272 mg KOH/g).

후처리

  1. customThe air was removed with three cycles of evacuation/nitrogen-fill
  2. customthe nitrogen sparge
  3. distillationAfter a 1-h hold, 159.3 g of distillate had been collected
  4. customto get
  5. customa clean separation
  6. temperatureThe temperature was increased to 180, 190, 200 and 210° C.
  7. customThe excess 2-phenylethanol (6.3% by GLC) was removed by vacuum distillation through a 15-cm Vigreux column at 140-165° C. (15-20 torr)
  8. distillationThe crude product was distilled at 150-155° C. (10 torr, 0.5 scfh nitrogen sweep)

출처 및 근거

ORD 기록
ord-6817493c9f4e42779169c07093b85fe9
출처 데이터셋
uspto-grants-2010_08
특허 번호
US07785573B2

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