1-Bromooctane → 3-Chloro-4-(octyloxy)benzoic acid

HRID 893249Notes

Reaction equation

HRID 893249 reaction equation
[Cl:1][C:2]1[C:3](O)=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([OH:7])=[O:6].[CH2:12](Br)[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19].[OH-:21].[K+]>C(O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[O:21][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])[C:5]([OH:7])=[O:6]

Participants

5

Reactant 3

HCID 81401-BromooctaneHCID 14797Potassium HydroxideHCID 745853-Chlorosalicylic acid

Product 1

HCID 189953693-Chloro-4-(octyloxy)benzoic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In 40 ml of ethanol were dissolved 10 g of 3-chlorohydroxybenzoic acid and 8 g of octyl bromide, and 40 ml a 2N aqueous solution of potassium hydroxide was added to the solution and the mixture was refluxed for 6 hours. The solution was made acidic and the precipitated crystal was recovered and recrystallized from an ethanol/water mixed solvent to obtain 9.5 g of 3-chloro-4-octyloxybenzoic acid.

Workup

  1. additionwas added to the solution
  2. temperaturethe mixture was refluxed for 6 hours
  3. customthe precipitated crystal was recovered
  4. customrecrystallized from an ethanol/water mixed solvent

Sources & evidence

ORD record
ord-d0d499c5ee7b450e955cd8dec7963588
Source dataset
uspto-grants-1992_06
Patent number
US05124069

Reaction notes

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