m-Chloroperbenzoic acid → HCID 21461390, compound

HRID 1941516Notes

Reaction equation

HRID 1941516 reaction equation
ClC1C=CC=C(C(OO)=[O:9])C=1.[CH3:12][C:13]12[C:19]([CH3:21])([CH3:20])[CH:16]([CH2:17][CH2:18]1)[CH2:15][C:14]2([CH2:23][C:24]([CH3:26])=[CH2:25])[OH:22].C(=O)(O)[O-].[Na+]>C(Cl)Cl>[CH3:12][C:13]12[C:19]([CH3:20])([CH3:21])[CH:16]([CH2:17][CH2:18]1)[CH2:15][C:14]2([CH2:23][C:24]1([CH3:26])[CH2:25][O:9]1)[OH:22]

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 13777456HCID 13777456, compound

Product 1

HCID 21461390HCID 21461390, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

38.0 g (0.22 mol) of m-chloroperbenzoic acid was added portionwise to a stirred and cooled (ice bath) suspension of 28.7 g (0.14 mol) of (1RS,2SR,4RS)-1,7,7-trimethyl-2-(2-methyl-2-propenyl)bicyclo[2.2.1]heptan-2-ol and 23.1 g (0.27 mol) of sodium bicarbonate in 500 ml of methylene chloride. The temperature was maintained below 20° C. The reaction mixture was stirred at room temperature for an additional 5 hours, filtered and washed with 300 ml of saturated aqueous sodium bicarbonate solution and 300 ml of brine. After drying with MgSO4 and evaporation of the solvent the crude epoxide (30.9 g) was used in the next step without further purification.

Workup

  1. temperaturecooled
  2. temperatureThe temperature was maintained below 20° C
  3. stirringThe reaction mixture was stirred at room temperature for an additional 5 hours
  4. filtrationfiltered
  5. washwashed with 300 ml of saturated aqueous sodium bicarbonate solution and 300 ml of brine
  6. dry with materialAfter drying with MgSO4 and evaporation of the solvent the crude epoxide (30.9 g)
  7. customwas used in the next step without further purification

Sources & evidence

ORD record
ord-470f09bb5b7d4dfe9d7e7d687809657e
Source dataset
uspto-grants-1997_12
Patent number
US05703250

Reaction notes

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