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

HRID 2352591Notes

Reaction equation

HRID 2352591 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 Hydroxide2×HCID 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. To the resulting reaction mixture was added an aqueous sodium hydroxide solution containing 2.4 g of sodium hydroxide, and the mixture was then further refluxed for 10 hours. After the reaction, the resulting reactioin solution was diluted with water, and the pH of the solution was adjusted to 2 by dropping hydrochloric acid. The resulting precipitate was corrected, sufficiently washed with water, and dried to obtain 10.8 g of the objective ether compound (Yield: 89 %).

Workup

  1. customTo the resulting reaction mixture
  2. temperaturethe mixture was then further refluxed for 10 hours
  3. customAfter the reaction
  4. washsufficiently washed with water
  5. customdried

Sources & evidence

ORD record
ord-c2c7ca0185c843ae9a8b64ee6d89d5b8
Source dataset
uspto-grants-1989_10
Patent number
US04877858

Reaction notes

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