m-Chloroperbenzoic acid → 3-Methoxy-1a,2,7,7a-tetrahydronaphtho[2,3-b]oxirene

HRID 542172Notes

Reaction equation

HRID 542172 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:4]=1[CH2:5][CH:6]=[CH:7][CH2:8]2.ClC1C=CC=C(C(OO)=[O:21])C=1>C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:4]=1[CH2:5][CH:6]1[O:21][CH:7]1[CH2:8]2

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 151310665-Methoxy-1,4-dihydronaphthalene

Product 1

HCID 151310673-Methoxy-1a,2,7,7a-tetrahydronaphtho[2,3-b]oxirene

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3.00 g (0.019M) of 1,4-dihydro-5-methoxynaphthalene are dissolved in 52 ml of methylene chloride, and cooled with an ice bath to 0°. 3.07 g (0.018M) of m-chloro-perbenzoic acid are subsequently added to this solution over the course of one minute. The ice bath is removed, and the reaction mixture is stirred for 15 hours at room temperature. The suspension is then added to a mixture of 20 ml of 10% sodium hydroxide and 40 g of ice. The organic phase is separated, and the aqueous phase is extracted twice, each time with 20 ml of methylene chloride. The combined organic phases are washed with water and sodium chloride solution, dried and concentrated by evaporation. 1a,2,7,7a-tetrahydro-3-methoxynaphth[2,3-b]oxirane is obtained (melting point 49.5°-50.5°, after purification by column chromatography, silica gel 0.063-0.200 mm, methylene chloride and recrystallisation from hexane).

Workup

  1. temperaturecooled with an ice bath to 0°
  2. customThe ice bath is removed
  3. additionThe suspension is then added to a mixture of 20 ml of 10% sodium hydroxide and 40 g of ice
  4. customThe organic phase is separated
  5. extractionthe aqueous phase is extracted twice
  6. washThe combined organic phases are washed with water and sodium chloride solution
  7. customdried
  8. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-d3b1537d68b549cfb2320e5ba56f3e13
Source dataset
uspto-grants-1987_04
Patent number
US04656167

Reaction notes

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