m-Chloroperbenzoic acid → HCID 12426268, compound

HRID 2355801Notes

Reaction equation

HRID 2355801 reaction equation
C(O[C:5]12[CH2:14][CH:9]3[CH2:10][CH:11]([CH2:13][C:7]([O:15]CC=C)([CH2:8]3)[CH2:6]1)[CH2:12]2)C=C.ClC1C=CC=C(C(OO)=[O:27])C=1>ClCCl>[C:7]12([OH:15])[CH2:8][CH:9]3[CH2:10][CH:11]([CH2:12][CH:5]([CH2:14]3)[CH:6]1[OH:27])[CH2:13]2

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 23113175HCID 23113175, compound

Product 1

HCID 12426268HCID 12426268, compoundYield 79.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The obtained 1,3-bis(2-propenyloxy)adamantane {5.96 g, yield: 80.1%, purity by gas chromatography: 96.0%, purity by gel permeation chromatography (hereinafter referred to as GPC): 99.5%} was dissolved in 30 ml of dichloromethane. Thereto was added 14.3 g (0.058 mol) of 70% m-chloroperbenzoic acid, followed by stirring at room temperature for 16 hours. Then, the reaction mixture was washed with 30 ml of a 25% aqueous sodium sulfite solution and further with water twice. The reaction mixture was subjected to distillation to remove dichloromethane, whereby was obtained crude 1,3-bis(glycidyloxy)adamantane {6.70 g, yield: 79.8% (from adamantanediol), purity by gas chromatography: 96.1%, GPC purity: 99.7%, colorless liquid}. The liquid was subjected to distillation at 0.1 mmHg at 140° C. to obtain, as a colorless transparent liquid, 1,3-bis(glycidyloxy)adamantane {5.36 g, yield: 63.8% (from adamantanediol), purity by gas chromatography: 98.3%, GPC purity: 99.8%}.

Workup

  1. washThen, the reaction mixture was washed with 30 ml of a 25% aqueous sodium sulfite solution and further with water twice
  2. distillationThe reaction mixture was subjected to distillation
  3. customto remove dichloromethane

Sources & evidence

ORD record
ord-712691913e214072a09c59256e050524
Source dataset
uspto-grants-2010_07
Patent number
US07754903B2

Reaction notes

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