m-Chloroperbenzoic acid → HCID 20196441, compound

HRID 652987Notes

Reaction equation

HRID 652987 reaction equation
[CH2:1]([O:8][CH2:9][C:10]1([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])[CH2:13][C:12](=[O:14])[CH2:11]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.ClC1C=CC=C(C(OO)=[O:41])C=1>C(Cl)Cl>[CH2:1]([O:8][CH2:9][C:10]1([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])[CH2:11][O:14][C:12](=[O:41])[CH2:13]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 57098043HCID 57098043, compound

Product 1

HCID 20196441HCID 20196441, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A stirred solution containing 2.27 g (5.1 mmol) of the compound prepared in (b) above and 2.2 g (12.75 mmol) of m-chloroperbenzoic acid in 30 ml of anhydrous methylene chloride was refluxed for 10 hours under a nitrogen atmosphere. The reaction mixture was then cooled to room temperature, washed with 10 ml of a 2M sodium bisulfite solution, washed twice with 10 ml of a 2M sodium bicarbonate solution and washed with 10 ml of brine, after which time it was dried over magnesium sulfate, filtered and evaporated to afford a colorless liquid. The liquid was then chromatographed on silica gel employing a mixture of petroleum ether and methyl-t-butyl ether in a ratio of 7:3 as the eluent to yield a colorless liquid.

Workup

  1. temperaturewas refluxed for 10 hours under a nitrogen atmosphere
  2. washwashed with 10 ml of a 2M sodium bisulfite solution
  3. washwashed twice with 10 ml of a 2M sodium bicarbonate solution
  4. washwashed with 10 ml of brine
  5. dry with materialafter which time it was dried over magnesium sulfate
  6. filtrationfiltered
  7. customevaporated
  8. customto afford a colorless liquid
  9. customThe liquid was then chromatographed on silica gel employing
  10. additiona mixture of petroleum ether and methyl-t-butyl ether in a ratio of 7:3 as the eluent
  11. customto yield a colorless liquid

Sources & evidence

ORD record
ord-8375fd6df8ac44b39d9abed683b34952
Source dataset
uspto-grants-1987_06
Patent number
US04673672

Reaction notes

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