Potassium Carbonate → 2-[2-([1,1'-Biphenyl]-4-yl)ethyl]oxirane

HRID 1390609Notes

Reaction equation

HRID 1390609 reaction equation
ClC1C=C(C(OO)=[O:9])C=CC=1.[CH2:12]([C:16]1[CH:21]=[CH:20][C:19]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[CH:18][CH:17]=1)[CH2:13][CH:14]=[CH2:15].C(=O)([O-])[O-].[K+].[K+]>ClCCl>[C:19]1([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:20]=[CH:21][C:16]([CH2:12][CH2:13][CH:14]2[CH2:15][O:9]2)=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 70297m-Chloroperbenzoic acidHCID 201456254-(But-3-en-1-yl)-1,1'-biphenyl

Product 1

HCID 1489402-[2-([1,1'-Biphenyl]-4-yl)ethyl]oxiraneYield 70.87%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred mixture of 88 parts of 3-chlorobenzeneperoxoic acid and 650 parts of dichloromethane are added dropwise 60 parts of 4-(3-butenyl)-1,1'-biphenyl. Upon completion, stirring is continued over week-end at room temperature. Then there are added dropwise 50 parts of a potassium carbonate solution. The organic phase is separated, washed with a sodium bisulfite solution and with water, dried, filtered and evaporated, yielding 63.5 parts (70.87%) of [2-([1,1'-biphenyl]-4-yl)ethyl]oxirane as an oily residue.

Workup

  1. waitis continued over week-end at room temperature
  2. customThe organic phase is separated
  3. washwashed with a sodium bisulfite solution and with water
  4. customdried
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-947a52d06e494cf29ca470c86c98a48e
Source dataset
uspto-grants-1979_02
Patent number
US04139540

Reaction notes

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