Hydrochloric Acid → HCID 19884404, compound

HRID 1577054Notes

Reaction equation

HRID 1577054 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[OH:11])[C:5]([OH:7])=[O:6].[CH2:12](Br)[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].[OH-].[K+].Cl>C(O)C>[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[O:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[C:5]([OH:7])=[O:6]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 123691-BromoheptaneHCID 14797Potassium Hydroxide2×HCID 843683-Bromo-4-hydroxybenzoic acid

Product 1

HCID 19884404HCID 19884404, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

25.8 g (0.119 mol) of the 3-bromo-4-hydroxybenzoic acid prepared in Step I was dissolved in 615 ml ethanol and 42.6 g (0.238 mol) of heptyl bromide was added to the solution. Aqueous potassium hydroxide (13.5 g of potassium hydroxide in 62 ml of water) was added with heating and the above solution was refluxed for ten hours. 125 ml of 10% aqueous potassium hydroxide was added and the solution was refluxed for two more hours. The reaction solution was allowed to stand to cool to room temperature, and excess 5 N hydrochloric acid solution was added commencing crystallization. The crystals were fractionated through filtration by suction, washed with water, dried and recrystallized with ethanol to yield 31.9 g of purified 3-bromo-4-n-heptyloxybenzoic acid. The yield was calculated to be 85.5%.

Workup

  1. temperaturewith heating
  2. temperaturethe above solution was refluxed for ten hours
  3. temperaturethe solution was refluxed for two more hours
  4. customcrystallization
  5. filtrationThe crystals were fractionated through filtration by suction
  6. washwashed with water
  7. customdried
  8. customrecrystallized with ethanol

Sources & evidence

ORD record
ord-8b12519e9f254bd8a93ee251c2f11819
Source dataset
uspto-grants-1981_09
Patent number
US04287085

Reaction notes

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