m-Chloroperbenzoic acid → HCID 70371397, compound

HRID 2166008Notes

Reaction equation

HRID 2166008 reaction equation
ClC1C=CC=C(C(OO)=[O:9])C=1.[CH2:12]([CH:15]1[CH2:20][CH2:19][C:18]([C:21]2[CH:26]=[CH:25][C:24]([CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])=[CH:23][CH:22]=2)=[CH:17][CH2:16]1)[CH2:13][CH3:14]>CCOCC>[CH2:27]([C:24]1[CH:25]=[CH:26][C:21]([C@H:18]2[CH2:19][CH2:20][C@H:15]([CH2:12][CH2:13][CH3:14])[CH2:16][C:17]2=[O:9])=[CH:22][CH:23]=1)[CH2:28][CH2:29][CH2:30][CH3:31]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 20032567HCID 20032567, compound

Product 1

HCID 70371397HCID 70371397, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

15 g of m-chloroperbenzoic acid are added at 0° to a solution of 20 g of p-(4-n-propylcyclohex-1-en-1-yl)-n-pentylbenzene (German Offenlegungsschrift 3,006,666) in 100 ml of ether, and the mixture is stirred for 16 hours. The reaction mixture is extracted several times with 10% sodium hydroxide solution, and the organic phase is dried with sodium sulfate. 40 ml of BF3 /ether complex (50% of BF3) are added to the resulting solution of epoxide, and the mixture is stirred for 5 minutes and is then poured onto ice. Working up in the customary manner gives trans-2-(p-n-pentylphenyl)-5-n-propylcyclohexanone. b.p. (0.1 mm Hg) 140°, c.p. -10°.

Workup

  1. extractionThe reaction mixture is extracted several times with 10% sodium hydroxide solution
  2. dry with materialthe organic phase is dried with sodium sulfate
  3. addition40 ml of BF3 /ether complex (50% of BF3) are added to the resulting solution of epoxide
  4. stirringthe mixture is stirred for 5 minutes
  5. additionis then poured onto ice

Sources & evidence

ORD record
ord-402936754a704c4298df5b5fcd497c55
Source dataset
uspto-grants-1990_07
Patent number
US04943384

Reaction notes

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