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

HRID 6321

Reaction equation

HRID 6321 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. Added thereto was an aqueous solution containing 2.4 g of sodium hydroxide, and reflux was further continued for 10 hours. After conclusion of the reaction, the reaction solution was diluted with water, and the pH of the diluted solution was lowered to 2 by dropping hydrochloric acid thereto. The generated precipitate was collected, and was then washed with water sufficiently and dried, to obtain 10.8 g of the objective ether compound. (Yield: 89%)

Workup

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

Sources & evidence

ORD record
ord-ef446ce9b28342d0a62b3c6f5e5e4b49
Source dataset
uspto-grants-1993_09
Patent number
US05248446

Linked notes

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