Hydrochloric Acid → HCID 21449501, compound

HRID 597021Notes

Reaction equation

HRID 597021 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)[CH:7]2[OH: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+]>[OH:18][CH: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 21449489HCID 21449489, compound

Product 1

HCID 21449501HCID 21449501, compound

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent2×

Procedure

2-Cyclopentyl-2-methyl-6,7-dichloroindan-1,5-diol (Example 5, Step C) (15.6 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 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 other 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 other solution with a 5% solution of sodium bicarbonate

Sources & evidence

ORD record
ord-c08954023c5f4e0782ddc062aa028dd2
Source dataset
uspto-grants-1977_03
Patent number
US04012524

Reaction notes

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