m-Chloroperbenzoic acid → HCID 13343700, compound

HRID 1154595Notes

Reaction equation

HRID 1154595 reaction equation
[Cl:1][C:2]1[C:7]([Cl:8])=[C:6]([C:9](=[O:17])[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[F:16])[CH:5]=[C:4]([CH:18]=[CH:19][CH3:20])[C:3]=1[OH:21].ClC1C=C(C=CC=1)C(OO)=[O:27]>C(Cl)Cl>[Cl:8][C:7]1[C:6]([C:9](=[O:17])[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[F:16])=[CH:5][C:4]2[CH2:18][CH:19]([CH2:20][OH:27])[O:21][C:3]=2[C:2]=1[Cl:1]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 53893713HCID 53893713, compound

Product 1

HCID 13343700HCID 13343700, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 2,3-dichloro-6-propenyl-4-(2-fluorobenzoyl)phenol (62.5 g., 0.192 mole) and m-chloroperoxybenzoic acid (47.6 g., 0.22 mole in 550 ml. of methylene chloride was stirred at room temperature for 24 hours. The precipitated m-chlorobenzoic acid was removed by filtration and the filtrate was washed successively with 5% aqueous sodium sulfite and 10% aqueous sodium bicarbonate. The methylene chloride was kept at room temperature for 4 days and then washed with 0.5N NaOH solution. After drying over MgSO4, the solvent was evaporated to give 45 g. of solid product, m.p. 148°-150° C.

Workup

  1. customThe precipitated m-chlorobenzoic acid was removed by filtration
  2. washthe filtrate was washed successively with 5% aqueous sodium sulfite and 10% aqueous sodium bicarbonate
  3. washwashed with 0.5N NaOH solution
  4. dry with materialAfter drying over MgSO4
  5. customthe solvent was evaporated
  6. customto give 45 g

Sources & evidence

ORD record
ord-a7ff008e952b4f2ebfe28347e369053d
Source dataset
uspto-grants-1984_12
Patent number
US04490384

Reaction notes

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