m-Chloroperbenzoic acid → 3,5-Bis-benzyloxy-4-(2-methyl-oxiranylmethyl)-benzoic acid tert-butyl ester

HRID 1177233Notes

Reaction equation

HRID 1177233 reaction equation
[C:1]([O:5][C:6](=[O:33])[C:7]1[CH:12]=[C:11]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:10]([CH2:21][C:22]([CH3:24])=[CH2:23])=[C:9]([O:25][CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH:8]=1)([CH3:4])([CH3:3])[CH3:2].C1C=C(Cl)C=C(C(OO)=[O:42])C=1>C(Cl)Cl>[C:1]([O:5][C:6](=[O:33])[C:7]1[CH:8]=[C:9]([O:25][CH2:26][C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)[C:10]([CH2:21][C:22]2([CH3:24])[CH2:23][O:42]2)=[C:11]([O:13][CH2:14][C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:12]=1)([CH3:2])([CH3:3])[CH3:4]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 595600213,5-Bis-benzyloxy-4-(2-methyl-allyl)-benzoic acid tert-butyl ester

Product 1

HCID 595604243,5-Bis-benzyloxy-4-(2-methyl-oxiranylmethyl)-benzoic acid tert-butyl esterYield 48.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3,5-bis-benzyloxy-4-(2-methyl-allyl)-benzoic acid tert-butyl ester (227a) (80 g, 0.18 mol) in CH2Cl2 (500 mL) was added m-CPBA (62 g, 0.36 mol) portion-wise. The mixture was refluxed overnight. The solid was filtered and washed with CH2Cl2. The filtrate was washed with saturated aqueous Na2S2O4 (250 mL) and brine (250 mL). The organic layer was separated, dried over Na2SO4 and concentrated to give a brown oil. The crude oil was quickly purified by column chromatography (EtOAc/petroleum ether=1/10) to give the title compound (40 g, 48.2% yield) as a white solid.

Workup

  1. temperatureThe mixture was refluxed overnight
  2. filtrationThe solid was filtered
  3. washwashed with CH2Cl2
  4. washThe filtrate was washed with saturated aqueous Na2S2O4 (250 mL) and brine (250 mL)
  5. customThe organic layer was separated
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated
  8. customto give a brown oil
  9. customThe crude oil was quickly purified by column chromatography (EtOAc/petroleum ether=1/10)

Sources & evidence

ORD record
ord-ed3dbf3c52da4bc68e5f42f8e6af0eff
Source dataset
uspto-grants-2010_11
Patent number
US07842713B2

Reaction notes

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