Benzyl Alcohol → Tetrahydro-5-[(phenylmethoxy)methyl]-2-furanmethanol

HRID 1278015

반응식

HRID 1278015 반응식
[CH2:1]([OH:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Na].[CH2:10]1[O:12][CH:11]1[CH2:13][CH2:14][CH:15]1[O:17][CH2:16]1>O>[C:2]1([CH2:1][O:8][CH2:16][CH:15]2[O:17][CH:11]([CH2:10][OH:12])[CH2:13][CH2:14]2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

5

반응물 3

HCID 244Benzyl AlcoholHCID 159031,2:5,6-DiepoxyhexaneHCID 5360545Sodium

생성물 1

HCID 12888742Tetrahydro-5-[(phenylmethoxy)methyl]-2-furanmethanol수율 48%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

100 ml of benzyl alcohol (0.97 mol) is cooled to 5° in an ice-bath and under a nitrogen atmosphere. 0.32 g of sodium (0.0139 mole; washed with hexane to remove the mineral oil) is slowly added to the rapidly stirred benzyl alcohol. The addition of the sodium is made at such a rate that the temperature remains below 20°. After the addition of the sodium has been completed the mixture is allowed to stir for 1/2 hour and slowly warmed to room temperature. Slowly, and with stirring 20 g of 1,5-hexadiene diepoxide (0.175 mole) is added to the mixture. After the addition of the diepoxide has been completed, the reaction mixture is heated at 150° for 16 hours. The mixture is then cooled to room temperature and with stirring is poured into 350 ml of water. The aqueous mixture is extracted with 2×250 ml portions of chloroform, the CHCl3 extracts are combined and dried over anhydrous sodium sulfate. The CHCl3 is removed in vacuo and the colorless oil vacuum distilled through a 10 cm vigreux distilling column. The fraction distilling at 151°-155° @0.5 mm is collected yielding 18.52 g (48%) of the above compound.

후처리

  1. washwashed with hexane
  2. customto remove the mineral oil)
  3. additionis slowly added to the rapidly stirred benzyl alcohol
  4. additionThe addition of the sodium
  5. customremains below 20°
  6. additionAfter the addition of the sodium
  7. additionis added to the mixture
  8. additionAfter the addition of the diepoxide
  9. temperaturethe reaction mixture is heated at 150° for 16 hours
  10. temperatureThe mixture is then cooled to room temperature
  11. stirringwith stirring
  12. extractionThe aqueous mixture is extracted with 2×250 ml portions of chloroform
  13. dry with materialdried over anhydrous sodium sulfate
  14. customThe CHCl3 is removed in vacuo
  15. distillationthe colorless oil vacuum distilled through a 10 cm
  16. distillationvigreux distilling column
  17. distillationThe fraction distilling at 151°-155° @0.5 mm
  18. customis collected

출처 및 근거

ORD 기록
ord-ed552daff7734c68b34b138f284d7092
출처 데이터셋
uspto-grants-1981_07
특허 번호
US04279902

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