Peracetic Acid → 3-([1,1'-Biphenyl]-4-ylmethyl)-6-oxabicyclo [3.1.0]hexane

HRID 65289Notes

Reaction equation

HRID 65289 reaction equation
[C:1]([O:4]O)(=O)[CH3:2].C([O-])(=O)C.[Na+].[CH:11]1([CH2:16][C:17]2[CH:22]=[CH:21][C:20]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[CH:19][CH:18]=2)CC=[CH:13][CH2:12]1.S(S([O-])=O)([O-])(=O)=O.[Na+].[Na+]>C(O)(=O)C.C(Cl)(Cl)Cl>[C:20]1([C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH:19]=[CH:18][C:17]([CH2:16][CH:11]2[CH2:2][CH:1]3[CH:13]([O:4]3)[CH2:12]2)=[CH:22][CH:21]=1

Participants

7

Reactant 4

HCID 6585Peracetic AcidHCID 517045Sodium AcetateHCID 656671Sodium PyrosulfiteHCID 202342694-(3-Cyclopenten-1-ylmethyl)-1,1'-biphenyl

Product 1

HCID 202342393-([1,1'-Biphenyl]-4-ylmethyl)-6-oxabicyclo [3.1.0]hexane

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6212ChloroformSolvent

Procedure

Peracetic acid in acetic acid (60 ml; 40%) was added over 5 min. to a cooled mixture of sodium acetate (8g) and 4-(3-cyclopenten-1-ylmethyl)-1,1'-biphenyl (20 g) in chloroform (150 ml). The mixture was stirred vigorously at room temperature for 4 h., then it was cooled and a solution of sodium metabisulphite was slowly added. The chloroform layer was washed with water, dilute sodium hydroxide solution, water and brine, dried and evaporated to give a 1:3 mixture (TLC) of two products (20 g). Crystallisation from methylene dichloride-ether gave two crops, rich in the slower running isomer (TLC). Recrystallisation from methylene dichloride/ether gave pure (±)-(1α,3α,5α)-3-([1,1'-biphenyl]-4-ylmethyl)-6-oxabicyclo[3.1.0]hexane (9.6 g), m.p. 130°-132° C.

Workup

  1. temperatureit was cooled
  2. washThe chloroform layer was washed with water, dilute sodium hydroxide solution, water and brine
  3. customdried
  4. customevaporated

Sources & evidence

ORD record
ord-c80d1a5254c34b05b04ee0370dcfcba0
Source dataset
uspto-grants-1986_09
Patent number
US04613619

Reaction notes

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