1-Bromooctane → 3'-Fluoro-4'-(octyloxy)[1,1'-biphenyl]-4-carboxylic acid

HRID 2372257Notes

Reaction equation

HRID 2372257 reaction equation
[OH-].[K+].[F:3][C:4]1[CH:5]=[C:6]([C:11]2[CH:16]=[CH:15][C:14]([C:17]([OH:19])=[O:18])=[CH:13][CH:12]=2)[CH:7]=[CH:8][C:9]=1[OH:10].Br[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28]>C(O)C>[F:3][C:4]1[CH:5]=[C:6]([C:11]2[CH:16]=[CH:15][C:14]([C:17]([OH:19])=[O:18])=[CH:13][CH:12]=2)[CH:7]=[CH:8][C:9]=1[O:10][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28]

Participants

5

Reactant 3

HCID 81401-BromooctaneHCID 14797Potassium HydroxideHCID 8361394-(3-Fluoro-4-hydroxyphenyl)benzoic acid

Product 1

HCID 189965163'-Fluoro-4'-(octyloxy)[1,1'-biphenyl]-4-carboxylic acidYield 86.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To 75 ml of an aqueous solution of 13% potassium hydroxide were added 120 ml of ethanol and 10 g (43.1 mmol) of the above 3'-fluoro-4'-hydroxybiphenyl-4-carboxylic acid, which were refluxed for 30 minutes and added with 25.0 g (129 mmol) of 1-bromooctane and then refluxed for 15 hours. After the air cooling, the precipitated crystal was filtered and recrystallized with acetic acid containing 5% hydrochloric acid and further with acetic acid to obtain 12.8 g (yield: 86.4%) of 3'-fluoro-4'-octyloxybiphenyl-4-carboxylic acid. This compound had the following properties:

Workup

  1. temperaturewere refluxed for 30 minutes
  2. temperaturerefluxed for 15 hours
  3. temperatureAfter the air cooling
  4. filtrationthe precipitated crystal was filtered
  5. customrecrystallized with acetic acid containing 5% hydrochloric acid and further with acetic acid

Sources & evidence

ORD record
ord-a14ede38e06445df8c3ae13078030387
Source dataset
uspto-grants-1992_03
Patent number
US05098602

Reaction notes

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