Hydrochloric Acid → 3-Chloro-4-(dodecyloxy)benzoic acid

HRID 1650647Notes

Reaction equation

HRID 1650647 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[Cl:11].[OH-].[Na+].[CH2:14](Br)[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25].Cl>CO.O1CCCC1.O>[CH2:25]([O:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[Cl:11])[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH3:14]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 89191-BromododecaneHCID 14798Sodium Hydroxide2×HCID 198603-Chloro-4-hydroxybenzoic acid

Product 1

HCID 197391753-Chloro-4-(dodecyloxy)benzoic acid

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

In a mixed solvent of methanol and tetrahydrofuran was dissolved 5.17 g of 4-hydroxy-3-chlorobenzoic acid, and a solution of 2.4 g of sodium hydroxide in 5 ml of water was added to the solution. Then, 10 ml of n-dodecyl bromide was added dropwise to the mixture and the resulting mixture was refluxed for 2 hours. Then, 1.2 g of sodium hydroxide was further added and the mixture was refluxed for 1 hour. The thus-obtained solution was put in a 1N aqueous solution of hydrochloric acid, and the precipitate was recovered and filtration, washed with water and then with n-hexane and recrystallized from ethyl acetate to obtain 4.1 g of 4-n-dodecyloxy-3-chlorobenzoic acid.

Workup

  1. temperaturethe resulting mixture was refluxed for 2 hours
  2. temperaturethe mixture was refluxed for 1 hour
  3. customthe precipitate was recovered
  4. filtrationfiltration
  5. washwashed with water
  6. customwith n-hexane and recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-c202068f9f654ce5906e378d2f21177f
Source dataset
uspto-grants-1990_05
Patent number
US04925591

Reaction notes

Loading…