Hydrochloric Acid → Tetrahydrothiopyran-4-carboxylic acid

HRID 2358451Notes

Reaction equation

HRID 2358451 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 702EthanolHCID 14798Sodium HydroxideHCID 21598641Thiane-4-carbonitrile

Product 1

HCID 21598642Tetrahydrothiopyran-4-carboxylic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

A solution of tetrahydro-thiopyran-4-carbonitrile (646 mmol), in ethanol (600 ml) was added in one portion to a rapidly stirring mixture of sodium hydroxide (258.4 g, 6.46 mol) in water (1.1 L). The mixture was then heated to 90° C. for 2 h, cooled to 0° C. and the pH adjusted to 2 with conc. hydrochloric acid solution. The ethanol was then removed in vacuo and the suspension extracted into dichloromethane (3×1 L). The combined organic extracts were then dried over magnesium sulfate and evaporated in vacuo to give tetrahydro-thiopyran-4-carboxylic acid as a brown solid (96 g, 646 mmol).

Workup

  1. temperaturecooled to 0° C.
  2. customThe ethanol was then removed in vacuo
  3. extractionthe suspension extracted into dichloromethane (3×1 L)
  4. dry with materialThe combined organic extracts were then dried over magnesium sulfate
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-1645f8ffc85c47cf841461264d66bfa5
Source dataset
uspto-grants-2010_07
Patent number
US07763732B2

Reaction notes

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