m-Chloroperbenzoic acid → Oxiranemethanol, 3-[(phenylmethoxy)methyl]-

HRID 1029985

反応式

HRID 1029985 の反応式
[CH2:1]([O:8][CH2:9][CH:10]=[CH:11][CH2:12][OH:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.ClC1C=CC=C(C(OO)=[O:22])C=1>ClCCl>[CH2:1]([O:8][CH2:9][CH:10]1[O:22][CH:11]1[CH2:12][OH:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

4

反応物 2

HCID 70297m-Chloroperbenzoic acidHCID 42282744-Benzyloxy-2-buten-1-ol

生成物 1

HCID 3934498Oxiranemethanol, 3-[(phenylmethoxy)methyl]-収率 99.1%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

7.13 g (0.04 mol) of 4-benzyloxy-2-buten-1-ol was dissolved in 250 ml of dichloromethane and 8.6 g (0.04 mol) of m-chloroperbenzoic acid (purity: 80%) was added thereto in four portions under ice-cooling and stirring. After stirring the mixture at the same temperature for additional 1 hour, the precipitate thus formed was filtered off. The filtrate was poured into a 10% aqueous solution of sodium hydrosulfite, extracted with dichloromethane, washed with water, and dried. After distilling off the solvent, the obtained liquid residue was purified by column chromatography (silica gel, hexane/ether) to thereby give 7.7 g of 4-benzyloxy-2,3-epoxybutan-1-ol as a colorless liquid.

後処理

  1. temperaturein four portions under ice-cooling
  2. stirringAfter stirring the mixture at the same temperature for additional 1 hour
  3. customthe precipitate thus formed
  4. filtrationwas filtered off
  5. additionThe filtrate was poured into a 10% aqueous solution of sodium hydrosulfite
  6. extractionextracted with dichloromethane
  7. washwashed with water
  8. customdried
  9. distillationAfter distilling off the solvent
  10. customthe obtained liquid residue was purified by column chromatography (silica gel, hexane/ether)

出典と根拠

ORDレコード
ord-9f8cf21fe04a4cfcbaf2c864048f6cc0
出典データセット
uspto-grants-1992_04
特許番号
US05102895

関連ノート

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