Hydrochloric Acid → 4-Heptyloxy-2-chlorobenzoic acid

HRID 437011Notes

Reaction equation

HRID 437011 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]([OH:11])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].Br[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19].[OH-].[K+].Cl>O.C(O)C>[CH2:13]([O:11][C:9]1[CH:8]=[CH:7][C:3]([C:4]([OH:6])=[O:5])=[C:2]([Cl:1])[CH:10]=1)[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 123691-BromoheptaneHCID 14797Potassium Hydroxide2×HCID 918212-Chloro-4-hydroxybenzoic acid

Product 1

HCID 40208144-Heptyloxy-2-chlorobenzoic acidYield 75%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent3×

Procedure

A mixture of 4.0 parts of 2-chloro-4-hydroxybenzoic acid, 8.3 parts of 1-bromoheptane, 2.6 parts of potassium hydroxide, 10 parts of water and 90 parts by volume of ethanol was refluxed for 20 hours. A solution of 2.5 parts of potassium hydroxide in 50 parts of water was then added and refluxing continued for an additional 1.5 hours. The reaction mixture was diluted with 100 parts of water, acidified with concentrated hydrochloric acid and extracted with methylene chloride. The combined extracts were dried over sodium sulfate, the solvent evaporated and the resultant residue recrystallized from hexane. 4.5 Parts of 4-heptyloxy-2-chlorobenzoic acid (75% yield) was obtained having a melting point of 76°-78° C.

Workup

  1. temperaturewas refluxed for 20 hours
  2. temperaturerefluxing
  3. extractionextracted with methylene chloride
  4. dry with materialThe combined extracts were dried over sodium sulfate
  5. customthe solvent evaporated
  6. customthe resultant residue recrystallized from hexane

Sources & evidence

ORD record
ord-2b5adc3c19c446858a5a7140b6c612b4
Source dataset
uspto-grants-1977_06
Patent number
US04029594

Reaction notes

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