Ethanol → HCID 69103239, compound

HRID 2220414Notes

Reaction equation

HRID 2220414 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5](CC#N)=[C:4]([O:11][CH:12]2[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]2)[CH:3]=1.[OH-:18].[K+].[CH2:20]([OH:22])[CH3:21]>O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:21][C:20]([OH:18])=[O:22])=[C:4]([O:11][CH:12]2[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]2)[CH:3]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 14797Potassium HydroxideHCID 69103961HCID 69103961, compound

Product 1

HCID 69103239HCID 69103239, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of (4-bromo-2-cyclohexyloxyphenyl)acetonitrile (1.45 g) and potassium hydroxide (829 mg) in ethanol (17.4 ml) and water (5 ml) was refluxed for 22 hours. Ethanol was removed by evaporation under reduced pressure. To the residue were added water and a mixture of hexane and ethyl acetate (1:1). After separation, the aqueous layer was adjusted below pH 3 with concentrated hydrochloric acid, and extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, evaporated and dried in vacuo to give (4-bromo-2-cyclohexyloxyphenyl)acetic acid (1.34 g).

Workup

  1. temperaturewas refluxed for 22 hours
  2. customEthanol was removed by evaporation under reduced pressure
  3. additionTo the residue were added water
  4. additiona mixture of hexane and ethyl acetate (1:1)
  5. customAfter separation
  6. extractionextracted with ethyl acetate
  7. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  8. customevaporated
  9. customdried in vacuo

Sources & evidence

ORD record
ord-0c1c12627fc64b19ba88853185f418cf
Source dataset
uspto-grants-2008_08
Patent number
US07417060B2

Reaction notes

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