Sodium Hydroxide → 5-Phenyl-6,6a-dihydro-1aH-indeno[1,2-b]oxirene

HRID 67818Notes

Reaction equation

HRID 67818 reaction equation
ClC1C=CC=C(C(OO)=[O:9])C=1.[C:12]1([C:18]2[CH:19]=[CH:20][CH:21]=[C:22]3[C:26]=2[CH2:25][CH:24]=[CH:23]3)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[OH-].[Na+].S([O-])([O-])(=O)=O.[Na+].[Na+]>C(Cl)(Cl)Cl>[O:9]1[CH:24]2[CH2:25][C:26]3[C:22]([CH:23]12)=[CH:21][CH:20]=[CH:19][C:18]=3[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 24436Sodium SulfateHCID 70297m-Chloroperbenzoic acidHCID 129423867-Phenyl-1H-indene

Product 1

HCID 132792805-Phenyl-6,6a-dihydro-1aH-indeno[1,2-b]oxireneYield 97.9%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

A stirred solution of 47.5 g (0.234 mole) of m-chloroperbenzoic acid (85% purity) in 390 ml of chloroform was cooled to 0° C. To this was added dropwise a solution of 45 g (0.234 mole) of 7-phenyl-1H-indene (which may be prepared as in Example 1G) in 110 ml of chloroform. After complete addition, the mixture was stirred for 21/2 hours, then was allowed to stand for 21 hours at 0° C. With the temperature in the range of 0°-5° C., 100 ml of a 10% aqueous solution of sodium hydroxide, then 50 ml of a 10% aqueous solution of sodium sulfate, were added dropwise with stirring. After complete addition the two-phase mixture was stirred for 30 minutes. The organic phase was separated, washed first with a dilute aqueous solution of sodium bicarbonate, then with water, dried over anhydrous sodium sulfate, and filtered. The filtrate was concentrated under reduced pressure to give 47.7 g of 1,2-epoxy-4-phenyindane as a pale yellow oil, 97% purity by gas chromatographic analysis.

Workup

  1. additionAfter complete addition
  2. waitto stand for 21 hours at 0° C
  3. stirringwith stirring
  4. additionAfter complete addition the two-phase mixture
  5. stirringwas stirred for 30 minutes
  6. customThe organic phase was separated
  7. washwashed first with a dilute aqueous solution of sodium bicarbonate
  8. dry with materialwith water, dried over anhydrous sodium sulfate
  9. filtrationfiltered
  10. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-24ac44474ffa4354bba5e9fe639851f8
Source dataset
uspto-grants-1982_08
Patent number
US04346251

Reaction notes

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