Hydrochloric Acid → HCID 59553197, compound

HRID 1171377Notes

Reaction equation

HRID 1171377 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([O:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])[CH:9]=1)[C:5]#N.C([OH:19])C.[OH-:20].[Na+].Cl>O>[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([O:10][CH:11]2[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]2)[CH:9]=1)[C:5]([OH:19])=[O:20]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 14798Sodium HydroxideHCID 66738074HCID 66738074, compound

Product 1

HCID 59553197HCID 59553197, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
75 °C

Procedure

A mixture of 3-fluoro-5-hexyloxybenzonitrile (1.0 g, 4.56 mmol), ethanol (12 ml), water (12 ml), and aq. NaOH (50%, 12 ml) is heated at 75° C. for 18 hours. The mixture is then cooled in an ice bath and acidified with concentrated HCl to pH 1. The mixture is extracted with ethyl acetate and the organic layer washed with brine, dried over Na2SO4, and concentrated to afford 3-fluoro-5-cyclohexyloxybenzoic acid as a yellow solid. MS: 239.11 (M+1).

Workup

  1. temperatureThe mixture is then cooled in an ice bath
  2. extractionThe mixture is extracted with ethyl acetate
  3. washthe organic layer washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-5766f07a359848cab23f69e34ce916f5
Source dataset
uspto-grants-2010_11
Patent number
US07829560B2

Reaction notes

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