Hydrochloric Acid → HCID 19884404, compound

HRID 1759493Notes

Reaction equation

HRID 1759493 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, compound

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 32.2 of purified 3-bromo-4-n-heptyloxybenzoic acid. The yield was calculated to be 85.9%.

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-cc99caa259684903b744da8c9c067603
Source dataset
uspto-grants-1982_07
Patent number
US04341652

Reaction notes

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