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

HRID 6315

Reaction equation

HRID 6315 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-4e95d25f5b2d41338d9ce44d7c9f9e29
Source dataset
uspto-grants-1993_09
Patent number
US05248446

Linked notes

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