Hydrochloric Acid → 4-Butoxy-2-chlorobenzoic acid

HRID 1154502Notes

Reaction equation

HRID 1154502 reaction equation
[OH-].[Na+].[Cl:3][C:4]1[CH:12]=[C:11]([OH:13])[CH:10]=[CH:9][C:5]=1[C:6]([OH:8])=[O:7].[CH2:14](I)[CH2:15][CH2:16][CH3:17].Cl>C(O)C.O>[Cl:3][C:4]1[CH:12]=[C:11]([O:13][CH2:14][CH2:15][CH2:16][CH3:17])[CH:10]=[CH:9][C:5]=1[C:6]([OH:8])=[O:7]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 10962Butyl iodideHCID 14798Sodium HydroxideHCID 918212-Chloro-4-hydroxybenzoic acid

Product 1

HCID 46924444-Butoxy-2-chlorobenzoic acidYield 71.7%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

9 g of caustic soda are dissolved in 200 ml of ethanol. To the thus-prepared solution there are added 17.25 g of 2-chloro-4-hydroxybenzoic acid and 18.4 g of butyl iodide. The resulting solution is heated at reflux under stirring for 5 hours, cooled, poured into 200 ml of water and acidified, to pH=1, with hydrochloric acid. The precipitate is filtered-off, washed with water and dried to give 16.4 g of ortho-chloro-para-n-butyoxybenzoic acid which is recrystallized from hexane. The yield of the recrystallized product is 13.8 g (60.5%), M.p. 92°-93° C.

Workup

  1. temperatureThe resulting solution is heated
  2. temperatureat reflux
  3. temperaturecooled
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-5b77c7a9d0a44fe0bab6cbe5eb269c13
Source dataset
uspto-grants-1984_12
Patent number
US04490277

Reaction notes

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