Hydrochloric Acid → HCID 23451931, compound

HRID 1277853Notes

Reaction equation

HRID 1277853 reaction equation
[CH2:1](Br)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[OH-].[K+].Cl.[Cl:11][C:12]1[CH:13]=[C:14]([CH:18]=[CH:19][C:20]=1[OH:21])[C:15]([OH:17])=[O:16]>C(O)C>[Cl:11][C:12]1[CH:13]=[C:14]([CH:18]=[CH:19][C:20]=1[O:21][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH3:6])[C:15]([OH:17])=[O:16]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 81011-BromohexaneHCID 14797Potassium Hydroxide2×HCID 198603-Chloro-4-hydroxybenzoic acid

Product 1

HCID 23451931HCID 23451931, compoundYield 77.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In accordance with step (2) of the reaction system 1.73 g of material A was dissolved in 50 ml of ethanol. 3.3 g of hexylbromide and potassium hydroxide (1.2 g KOH+5 ml H2O) was added and the mixture heated under reflux conditions for 10 hours. Following reflux, a 10% potassium hydroxide solution was added and the mixture refluxed for 2 hours. The mixture was hydrolyzed and then added to dilute hydrochloric acid to promote crystalization. The crystals were washed with water to yield 2 g of 3-chloro-4-n-hexyloxybenzoic acid (hereinafter referred to as material B'). The benzoic acid B' had a melting point of 140° C. and the absorption spectrum is illustrated in FIG. 5.

Workup

  1. temperaturethe mixture heated under reflux conditions for 10 hours
  2. temperatureFollowing reflux
  3. temperaturethe mixture refluxed for 2 hours
  4. customcrystalization
  5. washThe crystals were washed with water

Sources & evidence

ORD record
ord-6393161ffbcc427cb90b39060e645181
Source dataset
uspto-grants-1981_07
Patent number
US04279771

Reaction notes

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