Potassium Hydroxide → 4-phenyltetrahydro-2H-pyran-4-carboxylic acid

HRID 1868884Notes

Reaction equation

HRID 1868884 reaction equation
[C:1]1([C:7]2([C:13]([O:15]C)=[O:14])[CH2:12][CH2:11][O:10][CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[K+]>CCO.C(OCC)C>[C:1]1([C:7]2([C:13]([OH:15])=[O:14])[CH2:8][CH2:9][O:10][CH2:11][CH2:12]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 20110318HCID 20110318, compound

Product 1

HCID 41385534-phenyltetrahydro-2H-pyran-4-carboxylic acidYield 80.3%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 3283Diethyl EtherSolvent

Procedure

Methyl 4-phenyl-tetrahydro-2H-pyran-4-carboxylate (15.4 g, 69.9 mmol) was dissolved in EtOH (100 mL). KOH (39.2 g, 699 mmol) was then added. The reaction mixture was then heated at reflux for 2 hours and then cooled to ambient temperature, diluted with 150 mL of diethyl ether, added to a separatory funnel, partitioned with water, washed 2 times with 50 mL of water, and separated. The aqueous layer was acidified to a pH of 2 with concentrated HCl and extracted with CHCl3 (3×100 mL), dried over Na2SO4, and concentrated in vacuo to give the title compound (11.58 g) as a light yellow solid. MS m/e=229 (M+Na)+.

Workup

  1. temperatureThe reaction mixture was then heated
  2. temperatureat reflux for 2 hours
  3. additionadded to a separatory funnel
  4. custompartitioned with water
  5. washwashed 2 times with 50 mL of water
  6. customseparated
  7. extractionextracted with CHCl3 (3×100 mL)
  8. dry with materialdried over Na2SO4
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e0fef08ef28d4902b83c67f48a2dd192
Source dataset
uspto-grants-2009_12
Patent number
US07635715B2

Reaction notes

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