Hydrochloric Acid → 6-(2-Methylphenyl)-tetrahydropyran-2-one

HRID 322984Notes

Reaction equation

HRID 322984 reaction equation
O=[C:2]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[CH3:15])[CH2:3][CH2:4][CH2:5][C:6]([OH:8])=[O:7].[OH-].[K+].[BH4-].[Na+].Cl>O.C(OCC)(=O)C>[CH3:15][C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=1[CH:2]1[O:7][C:6](=[O:8])[CH2:5][CH2:4][CH2:3]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 27600035-(2-Methylphenyl)-5-oxovaleric acidHCID 4311764Sodium borohydride

Product 1

HCID 220102606-(2-Methylphenyl)-tetrahydropyran-2-oneYield 57.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a stirred suspension of 5-oxo-5-(2-methylphenyl)pentanoic acid (10 g) in water (100 mL) is added potassium hydroxide pellets (6.35 g). The temperature of the mixture is maintained at 2-20° C. whilst sodium borohydride (1.47 g) is added over 15 minutes. The reaction mixture is left at room temperature for 18 hours when 1 N hydrochloric acid (100 mL) is cautiously added followed by water (50 mL) and ethyl acetate (100 mL). The organic phase is separated and the aqueous phase extracted twice with ethyl acetate (100 mL). The combined organic phases are washed with brine (100 mL), dried over magnesium sulphate and evaporated to give 6-(2-methylphenyl)-tetrahydropyran-2-one (5.27 g) as a yellow oil.

Workup

  1. additionis added over 15 minutes
  2. additionis cautiously added
  3. customThe organic phase is separated
  4. extractionthe aqueous phase extracted twice with ethyl acetate (100 mL)
  5. washThe combined organic phases are washed with brine (100 mL)
  6. dry with materialdried over magnesium sulphate
  7. customevaporated

Sources & evidence

ORD record
ord-749333699eed48ccbc5c23500853bba6
Source dataset
uspto-grants-2001_04
Patent number
US06211234B1

Reaction notes

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