Peracetic Acid → (3-Phenyloxiranyl)methanol

HRID 843374

Reaction equation

HRID 843374 reaction equation
C(=O)([O-])[O-:2].[Na+].[Na+].[CH2:7]([OH:16])/[CH:8]=[CH:9]/[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C(OO)(=O)C.S([O-])([O-])=O.[Na+].[Na+]>O.C(Cl)Cl>[O:2]1[CH:9]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:8]1[CH2:7][OH:16]

Participants

7

Reactant 4

HCID 6585Peracetic Acid2×HCID 10340Sodium CarbonateHCID 24437Sodium SulfiteHCID 5315892Cinnamyl Alcohol

Product 1

HCID 89553(3-Phenyloxiranyl)methanol

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
17.5 °C

Procedure

Sodium carbonate (224 g) and trans-cinnamyl alcohol (200.0 g) were mixed with 2 L of methylene chloride, a slow nitrogen sweep was maintained through the vapor space of the flask and the mixture was cooled to 15-20° C. with a cold water bath. Peracetic acid solution (35%, 381.2 mL) was added over a 3 hour period, maintaining the internal temperature below 25° C. After the peracetic acid addition was complete, the mixture was stirred for 2-3 hours until complete, as shown by HPLC analysis. The mixture was cooled to 10° C. with an ice bath, and a solution of sodium sulfite (160 g) in 1200 ml water was added slowly over 90 minutes, keeping the temperature below 30° C. The phases were separated and the aqueous phase was extracted with methylene chloride (200 mL) to give a solution of the title compound.

Workup

  1. temperaturea slow nitrogen sweep was maintained through the vapor space of the flask
  2. temperaturemaintaining the internal temperature below 25° C
  3. temperatureThe mixture was cooled to 10° C. with an ice bath
  4. customthe temperature below 30° C
  5. customThe phases were separated
  6. extractionthe aqueous phase was extracted with methylene chloride (200 mL)

Sources & evidence

ORD record
ord-9efba723aa8449eabeb4caeeebe8fd59
Source dataset
uspto-grants-2002_04
Patent number
US06376711B1

Linked notes

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