Benzyl Alcohol → 2-Furancarboxylic acid, tetrahydro-, phenylmethyl ester

HRID 1708565

반응식

HRID 1708565 반응식
[O:1]1[CH2:5][CH2:4][CH2:3][CH:2]1[C:6](Cl)=[O:7].[CH2:9]([OH:16])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.N1C=CC=CC=1>CCOCC>[O:1]1[CH2:5][CH2:4][CH2:3][CH:2]1[C:6]([O:16][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:7]

참가 물질

5

반응물 3

HCID 244Benzyl AlcoholHCID 1049PyridineHCID 551254Tetrahydro-2-furancarbonyl chloride

생성물 1

HCID 112872082-Furancarboxylic acid, tetrahydro-, phenylmethyl ester

시약·촉매·용매 1

HCID 3283Diethyl Ether용매

실험 절차

Tetrahydrofuroyl chloride (15.0 g, 112 mmol) was added dropwise to a cold solution of benzyl alcohol (10.9 g, 101 mmol) and pyridine (20.0 g, 253 mmol) in Et2O (200 mL). The solution was stirred at 0° for 40 minutes, then filtered to remove the side product pyridine hydrochloride. The filtrate was washed with 0.1M HCl (50 mL), saturated aqueous NaHCO3 (50 mL), and brine (50 mL), and then dried over MgSO4. Filtration and evaporation of the solvent gave a yellow oil, which was distilled. Benzyl tetrahydrofuroate was obtained as a colorless oil (21.1 g), b.p. 118° to 120° at 0.5 mm Hg. Microanalysis calc'd for C12H14O3 (206.2): C, 69.89; H, 6.84; O, 23.27; Found: C, 69.62; H, 6.89.

후처리

  1. filtrationfiltered
  2. customto remove the side product pyridine hydrochloride
  3. washThe filtrate was washed with 0.1M HCl (50 mL), saturated aqueous NaHCO3 (50 mL), and brine (50 mL)
  4. dry with materialdried over MgSO4
  5. filtrationFiltration and evaporation of the solvent
  6. customgave a yellow oil, which
  7. distillationwas distilled

출처 및 근거

ORD 기록
ord-b3e1060bd6f9438ab665a221ca63788e
출처 데이터셋
uspto-grants-1994_10
특허 번호
US05359077

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