Hydrochloric Acid → Tetrahydrothiopyran-4-carboxylic acid

HRID 460680

Reaction equation

HRID 460680 reaction equation
[S:1]1[CH2:6][CH2:5]C(C#N)[CH2:3][CH2:2]1.[OH-:9].[Na+].Cl.[CH2:12]([OH:14])[CH3:13]>O>[S:1]1[CH2:6][CH2:5][CH:13]([C:12]([OH:9])=[O:14])[CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 702Ethanol2×HCID 14798Sodium HydroxideHCID 21598641Thiane-4-carbonitrile

Product 1

HCID 21598642Tetrahydrothiopyran-4-carboxylic acidYield 60%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 1.97 g (15.5 mmol) of tetrahydro-thiopyran-4-carbonitrile in 5 mL of ethanol (EtOH) was added to a solution of 6.2 g (155 mmol) of sodium hydroxide (NaOH) in 30 mL of EtOH and 15 mL of water, and the resulting mixture was heated at reflux for 4 h. The reaction mixture was cooled in an ice bath, acidified with concentrated hydrochloric acid to pH=2, and then concentrated to give a precipitate which was filtered to afford 1.36 g (60%) of desired tetrahydro-thiopyran-4-carboxylic acid as a brown crystalline solid as indicated by 1H NMR.

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureat reflux for 4 h
  3. temperatureThe reaction mixture was cooled in an ice bath
  4. concentrationconcentrated
  5. customto give a precipitate which
  6. filtrationwas filtered

Sources & evidence

ORD record
ord-7dece2fd7d37467bbf55b4ed9dc15e04
Source dataset
uspto-grants-2007_03
Patent number
US07196111B2

Linked notes

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