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

HRID 1939705
ノート
印刷プレビュー

反応式

HRID 1939705 の反応式
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
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 67553Tetrabutylammonium Iodide触媒

反応条件

温度
110 °C

実験手順

(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.

後処理

  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.)

出典と根拠

ORDレコード
ord-e482a6f881814f8e95a21ddcd39d8aa3
出典データセット
uspto-grants-1997_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05696263

反応ノート

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