Potassium Carbonate → HCID 178434805, compound

HRID 2073146Notes

Reaction equation

HRID 2073146 reaction equation
ClC1C=CC=C(C(OO)=[O:9])C=1.C(=O)([O-])[O-].[K+].[K+].[CH2:18]([C@H:23]1[CH2:28][CH2:27][C@H:26]([C:29]2[CH:36]=[CH:35][C:32]([C:33]#[N:34])=[CH:31][CH:30]=2)[CH2:25][CH2:24]1)[CH2:19][CH:20]=[CH:21][CH3:22]>C(Cl)Cl>[O:9]1[CH:21]([CH3:22])[CH:20]1[CH2:19][CH2:18][C@H:23]1[CH2:24][CH2:25][C@H:26]([C:29]2[CH:36]=[CH:35][C:32]([C:33]#[N:34])=[CH:31][CH:30]=2)[CH2:27][CH2:28]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 70297m-Chloroperbenzoic acid2×HCID 178444326HCID 178444326, compound

Product 1

HCID 178434805HCID 178434805, compoundYield 99.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 4.49 g of 90% m-chloroperbenzoic acid in 100 ml of methylene chloride was treated with 11.3 g of powdered potassium carbonate. The mixture was treated dropwise at 0° C. within 5 minutes with a solution of 5.93 g of p-[trans-4-(3-pentenyl)cyclohexyl]benzonitrile in 20 ml of methylene chloride and stirred at room temperature for 2 hours. The mixture was subsequently treated with another 4.49 g of 90% m-chloroperbenzoic acid and the resulting mixture was stirred further. After a total of 70 hours, the reaction mixture was partitioned three times in methylene chloride/10% sodium thiosulphate solution. The organic extracts were washed with sodium thiosulphate solution and water, dried over magnesium sulphate, filtered and concentrated. Chromatographic separation of the resulting, light yellowish oil (6.3 g) on silica gel with ethyl acetate/petroleum ether (vol. 10:90) gave 6.27 g (99.5%) of p-[trans-4-(3,4-epoxypentyl)cyclohexyl]benzonitrile as a colourless oil.

Workup

  1. stirringthe resulting mixture was stirred further
  2. customAfter a total of 70 hours, the reaction mixture was partitioned three times in methylene chloride/10% sodium thiosulphate solution
  3. washThe organic extracts were washed with sodium thiosulphate solution and water
  4. dry with materialdried over magnesium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customChromatographic separation of the resulting, light yellowish oil (6.3 g) on silica gel with ethyl acetate/petroleum ether (vol. 10:90)

Sources & evidence

ORD record
ord-47fb77652d384a3cae31c945442a274c
Source dataset
uspto-grants-1990_04
Patent number
US04915480

Reaction notes

Loading…