Hydrochloric Acid → HCID 67078060, compound

HRID 1475642Notes

Reaction equation

HRID 1475642 reaction equation
[OH-].[Na+].C([C:5]([C:14]1[CH:19]=[CH:18][C:17]([Br:20])=[CH:16][CH:15]=1)([CH:9]1[CH2:13][CH2:12][CH2:11][CH2:10]1)[C:6]([O-:8])=[O:7])C.O.Cl>CO>[Br:20][C:17]1[CH:16]=[CH:15][C:14]([CH:5]([CH:9]2[CH2:13][CH2:12][CH2:11][CH2:10]2)[C:6]([OH:8])=[O:7])=[CH:19][CH:18]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 131732782HCID 131732782, compound

Product 1

HCID 67078060HCID 67078060, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

386 ml (96.4 mmol) of 10% strength aqueous sodium hydroxide solution were added to a solution of 30 g (96.4 mmol) of (+/−)-ethyl(4-bromophenyl)(cyclopentyl)acetate in 655 ml of methanol, and the mixture was heated under reflux for 3 h. After cooling, the solution was stirred into 2 liters of water, adjusted to pH 1-2 by addition of dilute hydrochloric acid and extracted with ethyl acetate. The organic phase was dried over magnesium sulphate and concentrated. This gave 27.2 g (92% of theory) of the title compound.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 3 h
  3. temperatureAfter cooling
  4. extractionextracted with ethyl acetate
  5. dry with materialThe organic phase was dried over magnesium sulphate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-89375bf02a444df1be23f69ed5d43d9f
Source dataset
uspto-grants-2015_04
Patent number
US09018258B2

Reaction notes

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