4-Hydroxybenzoic Acid → 4-(Nonyloxy)benzoic acid

HRID 1602035Notes

Reaction equation

HRID 1602035 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=1.[CH2:11](Br)[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19].[OH-].[K+].Cl>O.C(O)C>[CH2:11]([O:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=1)[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19]

Participants

7

Reactant 4

HCID 1354-Hydroxybenzoic AcidHCID 313Hydrochloric AcidHCID 127421-BromononaneHCID 14797Potassium Hydroxide

Product 1

HCID 1399924-(Nonyloxy)benzoic acidYield 75%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

12.7 Grams (0.0917 mol) of p-hydroxybenzoic acid, 28.5 g of n-nonyl bromide and 10.2 g of potassium hydroxide were added to a mixture composed of 1,500 ml (milliliter) of ethanol and 200 ml of water, and the mixture was allowed to react under reflux for 10 hours. Further, 500 ml of water was added thereto, and the mixture was stirred for 3 hours. After the completion of the reaction, a concentrated hydrochloric acid was added to acidify the reaction mixture. Thereafter, the solvent was distilled off, and the remaining product was cooled to room temperature and then filtered to give a colorless solid. The solid was fully washed with water and re-crystallized from chloroform to give an intended product (yield 75%).

Workup

  1. customto react
  2. temperatureunder reflux for 10 hours
  3. customAfter the completion of the reaction
  4. distillationThereafter, the solvent was distilled off
  5. filtrationfiltered
  6. customto give a colorless solid
  7. washThe solid was fully washed with water
  8. customre-crystallized from chloroform

Sources & evidence

ORD record
ord-f8920dc7f37d466db345d360cdbf6b43
Source dataset
uspto-grants-1999_11
Patent number
US05980780

Reaction notes

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