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

HRID 1029985

Reaction equation

HRID 1029985 reaction equation
[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

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-9f8cf21fe04a4cfcbaf2c864048f6cc0
Source dataset
uspto-grants-1992_04
Patent number
US05102895

Linked notes

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