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Benzyl Bromide → (S)-4-Benzyloxy-1,2-butanediol

HRID 1939705
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HRID 1939705 반응식
C(C1(C(C)C)[O:8][C@@H:7]([CH2:9][CH2:10][OH:11])[CH2:6][O:5]1)(C)C.[CH2:15](Br)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[OH-].[Na+]>[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH2:15]([O:11][CH2:10][CH2:9][C@H:7]([OH:8])[CH2:6][OH:5])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1
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참가 물질

5

반응물 3

HCID 7498Benzyl BromideHCID 14798Sodium HydroxideHCID 54467051(S)-4-(2-Hydroxyethyl)-2,2-diisopropyl-1,3-dioxolane

생성물 1

HCID 9794180(S)-4-Benzyloxy-1,2-butanediol수율 92.3%

시약·촉매·용매 1

HCID 67553Tetrabutylammonium Iodide촉매

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온도
110 °C

실험 절차

(S)-2,2-Diisopropyl-4-(2-hydroxyethyl)dioxolane (76.2 g, 0.377 mol), benzylbromide (129 g, 0.753 mol) and tetrabutylammonium iodide (7 g, 19 mmol) were mixed with a concentrated sodium hydroxide solution (40 g in 90 mL of water, 2.26 mol) in a 3-neck flask equipped with a mechanic stirrer and a condenser. After stirred at 110° C. for 18 hours, the mixture was cooled to room temperature and the organic layer was separated. The aqueous layer was extracted with methylene chloride (100 mL×2). The combined methylene chloride extrats were dried over magnesium sulfate. The solvent was evaporated, and the residue was treated with 300 mL of 1.5M sulfuric acid. After stirred at 100° C. for 8 hours, the mixture was cooled to room temperature, and hexane (300 mL) was added. The aqueous layer was washed with hexane twice (200 mL×2), and then ajusted pH to 8-9 with concentrated sodium sodium hydroxide. The solution was extrated with ethyl acetate (200 mL×3). The combined ethyl acetate extrates were dried over magnesium sulfate. The solvent was evaporated, and the residue was purified by fractional distillation in vacuo (0.1 mmHg, bp 150°-170° C.) to give 68.3 g (92% yield) of the title compound as an oil.

후처리

  1. customequipped with a mechanic stirrer and a condenser
  2. temperaturethe mixture was cooled to room temperature
  3. customthe organic layer was separated
  4. extractionThe aqueous layer was extracted with methylene chloride (100 mL×2)
  5. dry with materialThe combined methylene chloride extrats were dried over magnesium sulfate
  6. customThe solvent was evaporated
  7. additionthe residue was treated with 300 mL of 1.5M sulfuric acid
  8. stirringAfter stirred at 100° C. for 8 hours
  9. temperaturethe mixture was cooled to room temperature
  10. additionhexane (300 mL) was added
  11. washThe aqueous layer was washed with hexane twice (200 mL×2)
  12. dry with materialThe combined ethyl acetate extrates were dried over magnesium sulfate
  13. customThe solvent was evaporated
  14. distillationthe residue was purified by fractional distillation in vacuo (0.1 mmHg, bp 150°-170° C.)

출처 및 근거

ORD 기록
ord-e482a6f881814f8e95a21ddcd39d8aa3
출처 데이터셋
uspto-grants-1997_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05696263

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