m-Chloroperbenzoic acid → HCID 21561498, compound

HRID 1581118Notes

Reaction equation

HRID 1581118 reaction equation
[OH:1][CH:2]1[CH2:6][CH2:5][CH:4]([CH:7]=[CH:8][CH:9]([OH:15])[CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])[CH:3]1[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][C:22]([O:24][CH3:25])=[O:23].ClC1C=CC=C(C(OO)=[O:34])C=1>ClCCl>[OH:1][CH:2]1[CH2:6][CH2:5][CH:4]([CH:7]2[O:34][CH:8]2[CH:9]([OH:15])[CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])[CH:3]1[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][C:22]([O:24][CH3:25])=[O:23]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 54187079Methyl 7-[2-hydroxy-5-(3-hydroxy-1-octenyl)cyclopentyl]heptanoate

Product 1

HCID 21561498HCID 21561498, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of methyl 7-[2-hydroxy-5-(3-hydroxy-1-octenyl)cyclopentyl]heptanoate (1.0 g.) [prepared as described in Example 5], metachlorperbenzoic acid (2.0 g.) and dichloromethane (30 ml.) was refluxed for days. The precipitated metachlorbenzoic acid was filtered from the cooled solution and washed with dichloromethane. The filtrate was washed successively with sodium sulphite solution, twice with 5% sodium bicarbonate solution and finally water, dried over sodium sulphate and evaporated to give methyl 7-[2-hydroxy-5-(3-hydroxy-1,2-epoxy-1-octyl)cyclopentyl]heptanoate (0.96 g.,92%), νmax 3450 cm-1, 1730 cm-1 and 1170 cm-1.

Workup

  1. filtrationThe precipitated metachlorbenzoic acid was filtered from the cooled solution
  2. washwashed with dichloromethane
  3. washThe filtrate was washed successively with sodium sulphite solution, twice with 5% sodium bicarbonate solution and finally water
  4. dry with materialdried over sodium sulphate
  5. customevaporated

Sources & evidence

ORD record
ord-79cec05e01ae488ead16616f98a82031
Source dataset
uspto-grants-1976_01
Patent number
US03935261

Reaction notes

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