Water → Ethyl p-(6-Bromohexyloxy)benzoate

HRID 359803Notes

Reaction equation

HRID 359803 reaction equation
[OH:1][C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][CH:3]=1.[OH-].[K+].[Br:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21]Br.O>CS(C)=O>[Br:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][O:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:11][CH:12]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8434EthylparabenHCID 123681,6-DibromohexaneHCID 14797Potassium Hydroxide

Product 1

HCID 18989362Ethyl p-(6-Bromohexyloxy)benzoateYield 71.4%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of 232 g of ethyl 4-hydroxybenzoate [XII; Alk=C2H5 ] in 1.2 liters of dimethylsulfoxide was added 100 g of potassium hydroxide. The mixture was stirred for five minutes, 678 g of 1,6-dibromohexane was then added, and the mixture stirred for four hours during which an exothermic reaction occurred (max. temp. 46° C.). The reaction mixture was added to 1500 ml of water and extracted three times with 800 ml of cyclohexane. The cyclohexane layer was washed with 800 ml of water, 200 ml 2N potassium hydroxide and 800 ml concentrated sodium chloride solution, then filtered and concentrated in vacuo. The residue was triturated with ether to give 328.1 g of ethyl 4-(6-bromohexyloxy)benzoate.

Workup

  1. stirringthe mixture stirred for four hours during which
  2. customan exothermic reaction
  3. custom(max. temp. 46° C.)
  4. extractionextracted three times with 800 ml of cyclohexane
  5. washThe cyclohexane layer was washed with 800 ml of water, 200 ml 2N potassium hydroxide and 800 ml concentrated sodium chloride solution
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was triturated with ether

Sources & evidence

ORD record
ord-7282f901de3d4d6c8715599be6f89aec
Source dataset
uspto-grants-1991_03
Patent number
US05002960

Reaction notes

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