Hydrochloric Acid → 4-[4-(Decyloxy)-3-fluorophenyl]-benzoic acid

HRID 1165731Notes

Reaction equation

HRID 1165731 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:9]2[CH:14]=[CH:13][C:12]([C:15]([OH:17])=[O:16])=[CH:11][CH:10]=2)[CH:5]=[CH:6][C:7]=1[OH:8].[CH2:18](Br)[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27].[OH-].[Na+].Cl>C(O)C>[CH2:18]([O:8][C:7]1[CH:6]=[CH:5][C:4]([C:9]2[CH:14]=[CH:13][C:12]([C:15]([OH:17])=[O:16])=[CH:11][CH:10]=2)=[CH:3][C:2]=1[F:1])[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 81731-BromodecaneHCID 14798Sodium HydroxideHCID 8361394-(3-Fluoro-4-hydroxyphenyl)benzoic acid

Product 1

HCID 147456314-[4-(Decyloxy)-3-fluorophenyl]-benzoic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The resulting 3'-fluoro-4'-hydroxybiphenyl-4-carboxylic acid was heated under reflux for 10 hours in hydrous ethanol together with 1.2 moles, per mole of the carboxylic acid, of decyl bromide and 1.95 moles, per mole of the carboxylic acid, of sodium hydroxide. Then, 10% hydrochloric acid was added to adjust the pH of the solution to 2 to 3. The solution was then heated under reflux for 1 hour. After cooling, the organic materials were extracted with chloroform. The chloroform layer was washed with water and dried over anhydrous sodium sulfate. The chloroform layer was concentrated to obtain crude crystals. Recrystallization from ethanol gave the desired 4'-decyloxy-3'-fluorobiphenyl-4-carboxylic acid. The yield in this alkoxylation reaction slightly varies depending upon the type of the alkyl bromide used, but it is generally 60 to 80%.

Workup

  1. temperatureThe solution was then heated
  2. temperatureunder reflux for 1 hour
  3. temperatureAfter cooling
  4. extractionthe organic materials were extracted with chloroform
  5. washThe chloroform layer was washed with water
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationThe chloroform layer was concentrated
  8. customto obtain crude crystals
  9. customRecrystallization from ethanol

Sources & evidence

ORD record
ord-96975ec4a9ab44a984a98b5c2f251512
Source dataset
uspto-grants-1990_03
Patent number
US04911862

Reaction notes

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