Hydrochloric Acid → HCID 13646820, compound

HRID 1287462Notes

Reaction equation

HRID 1287462 reaction equation
[CH:1]1([C:6]2([CH3:19])[CH2:14][C:13]3[C:8](=[C:9]([Cl:17])[C:10]([Cl:16])=[C:11]([OH:15])[CH:12]=3)[C:7]2=[O:18])[CH2:5][CH2:4][CH2:3][CH2:2]1.[C:20]1(=[O:24])[O:23][CH2:22][CH2:21]1.Cl>[OH-].[Na+]>[O:18]=[C:7]1[C:8]2[C:13](=[CH:12][C:11]([O:15][CH2:22][CH2:21][C:20]([OH:24])=[O:23])=[C:10]([Cl:16])[C:9]=2[Cl:17])[CH2:14][C:6]1([CH:1]1[CH2:2][CH2:3][CH2:4][CH2:5]1)[CH3:19]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 2365Beta-PropiolactoneHCID 123955886,7-Dichloro-2-cyclopentyl-5-hydroxy-2-methylindan-1-one

Product 1

HCID 13646820HCID 13646820, compound

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent2×

Procedure

2-Cyclopentyl-2-methyl-5-hydroxy-6,7-dichloro-1-indanone (15.5 g., 0.05 mole) is dissolved in a 10% sodium hydroxide solution (50 ml.). The solution is heated to reflux and beta-propiolactone (36.0 g., 0.5 mole) is added at such a rate as to keep the reaction mixture refluxing. The reaction mixture is kept basic by the addition of 10% sodium hydroxide. The reaction mixture is cooled and acidified with dilute hydrochloric acid. The product is extracted with ether and extracted from the ether solution with a 5% solution of sodium bicarbonate. Acidification affords the desired product.

Workup

  1. temperatureThe solution is heated
  2. temperatureto reflux
  3. temperaturerefluxing
  4. temperatureThe reaction mixture is cooled
  5. extractionThe product is extracted with ether
  6. extractionextracted from the ether solution with a 5% solution of sodium bicarbonate

Sources & evidence

ORD record
ord-19c588f040084734a3b747b856e1a94a
Source dataset
uspto-grants-1976_10
Patent number
US03984465

Reaction notes

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