Hydrochloric Acid → 4-(7-Octenyloxy)benzoic acid

HRID 1612582Notes

Reaction equation

HRID 1612582 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH:8]=[CH2:9].[OH:10][C:11]1[CH:21]=[CH:20][C:14]([C:15]([O:17]CC)=[O:16])=[CH:13][CH:12]=1.C(=O)([O-])[O-].[K+].[K+].[OH-].[Na+].Cl>C(O)C.O>[CH2:2]([O:10][C:11]1[CH:21]=[CH:20][C:14]([C:15]([OH:17])=[O:16])=[CH:13][CH:12]=1)[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH:8]=[CH2:9]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 8434EthylparabenHCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 759078-Bromooct-1-ene

Product 1

HCID 139976794-(7-Octenyloxy)benzoic acidYield 89%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

9.4 g of 8-bromo-1-octene, 9.0 g of ethyl p-hydroxybenzoate, and 7.6 g of potassium carbonate were refluxed in ethanol for 10 hours. Thereto added was an aqueous solution containing 2.4 g of sodium hydroxide, and then reflux was further continued for 10 hours. After conclusion of the reaction, the reaction solution was diluted with water, and the pH of the solution was lowered to 2 by dropping hydrochloric acid. The generated precipitate was collected, washed sufficiently with water, and dried, to obtain 10.8 g of the objective ether compound. (Yield: 89%)

Workup

  1. additionThereto added
  2. temperaturereflux
  3. customAfter conclusion of the reaction
  4. customThe generated precipitate was collected
  5. washwashed sufficiently with water
  6. customdried
  7. customto obtain 10.8 g of the objective ether compound

Sources & evidence

ORD record
ord-488841faf8524eb5b56e415e4aa4a1cf
Source dataset
uspto-grants-1993_03
Patent number
US05190686

Reaction notes

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