Hydrochloric Acid → 1,4-Dioxaspiro[4.5]decane-8-carboxylic acid, 8-(4-fluorophenyl)-

HRID 2370294Notes

Reaction equation

HRID 2370294 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:18]#N)[CH2:17][CH2:16][C:11]3([O:15][CH2:14][CH2:13][O:12]3)[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[OH-:20].[K+].[OH2:22].Cl>C(O)CO>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:18]([OH:22])=[O:20])[CH2:17][CH2:16][C:11]3([O:15][CH2:14][CH2:13][O:12]3)[CH2:10][CH2:9]2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14797Potassium HydroxideHCID 122302421,4-Dioxaspiro[4.5]decane-8-carbonitrile, 8-(4-fluorophenyl)-

Product 1

HCID 122302461,4-Dioxaspiro[4.5]decane-8-carboxylic acid, 8-(4-fluorophenyl)-

Reagents, catalysts & solvents 1

HCID 174Ethylene GlycolSolvent

Procedure

30.1 g of 8-(4-Fluoro-phenyl)-1,4-dioxa-spiro[4.5]decane-8-carbonitrile (74) were dissolved in 91 mL of ethylene glycol. 19.4 g of powdered potassium hydroxide were added and the mixture was heated to reflux until conversion was complete. The mixture was allowed to cool down to room temperature and poured into 300 mL of water. The pH was adjusted to 4 by addition of 2N HCl and the aqueous layer was extracted With ethyl acetate. The organic layer was extracted with brine, dried over magnesium sulfate and evaporated to dryness to give 29.85 g of the desired product. Rt=1.81 min (Method B). Detected mass: 281.2 (M+H+).

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux until conversion
  3. extractionthe aqueous layer was extracted With ethyl acetate
  4. extractionThe organic layer was extracted with brine
  5. dry with materialdried over magnesium sulfate
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-e3be8928a63b4a21a7114ee0bb840827
Source dataset
uspto-grants-2014_04
Patent number
US08710077B2

Reaction notes

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