m-Chloroperbenzoic acid → HCID 20305773, compound

HRID 1732253Notes

Reaction equation

HRID 1732253 reaction equation
[CH2:1]([O:8][CH2:9][CH:10]([CH3:23])[CH2:11][CH2:12][CH2:13][C:14]([CH3:22])=[CH:15][CH2:16][CH2:17][C:18](=[O:21])[CH2:19][Br:20])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.ClC1C=CC=C(C(OO)=[O:32])C=1>C(Cl)Cl>[CH2:1]([O:8][CH2:9][CH:10]([CH3:23])[CH2:11][CH2:12][CH2:13][C:14]1([CH3:22])[O:32][CH:15]1[CH2:16][CH2:17][C:18](=[O:21])[CH2:19][Br:20])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 54208735HCID 54208735, compound

Product 1

HCID 20305773HCID 20305773, compoundYield 107.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

11-Benzyloxy-1-bromo-6,10-dimethyl-2-oxo-undec-5-ene (15.6 g, 41 mM) in methylene chloride (250 ml) is treated with 85% m-chloroperbenzoic acid (8.35 g, 41 mM) in methylene chloride (200 ml) at 0° C. for 3 hours. The reaction mixture is washed with brine, saturated sodium sulfite, brine and then dried (Na2SO4). The solvent is removed in vacuo to give crude 11-benzyloxy-1-bromo-6,10-dimethyl-5,6-epoxy-undecan-2-one (17.5 g).

Workup

  1. washThe reaction mixture is washed with brine, saturated sodium sulfite, brine
  2. dry with materialdried (Na2SO4)
  3. customThe solvent is removed in vacuo

Sources & evidence

ORD record
ord-57d92361dc344614909f2e07af94a7a1
Source dataset
uspto-grants-1980_12
Patent number
US04237055

Reaction notes

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