Hydrochloric Acid → 2-(4'-Methoxy-biphenyl-4-ylsulfanyl)-acetic acid

HRID 1370683Notes

Reaction equation

HRID 1370683 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][C:12]([SH:15])=[CH:11][CH:10]=2)=[CH:5][CH:4]=1.Br[CH2:17][C:18]([O:20]CC)=[O:19].[OH-].[K+].Cl>C(O)C.O>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]2[CH:14]=[CH:13][C:12]([S:15][CH2:17][C:18]([OH:20])=[O:19])=[CH:11][CH:10]=2)=[CH:7][CH:8]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 7748Ethyl bromoacetateHCID 14797Potassium Hydroxide2×HCID 27597244'-Methoxy-biphenyl-4-thiol

Product 1

HCID 185104422-(4'-Methoxy-biphenyl-4-ylsulfanyl)-acetic acidYield 77.2%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 962WaterSolvent

Procedure

To a solution of 4.30 g of 4′-methoxy-biphenyl-4-thiol and 3.34 g of ethyl 2-bromo-acetate in 10 ml of ethanol was added over 5 min a solution of 1.12 g of potassium hydroxide in 20 ml of ethanol. The reaction mixture was stirred at 20° for 4 h and then, 1.68 g of potassium hydroxide and 3 ml of water were added and stirring was continued for 15 h at 20°. The mixture was poured onto 150 ml of ice/water and the pH of the mixture set to 2 by the addition of 3N hydrochloric acid. The precipitate was collected by filtration, washed with water and dried to give 4.21 g of 2-(4′-methoxy-biphenyl-4-ylsulfanyl)-acetic acid as white crystals.

Workup

  1. stirringstirring
  2. waitwas continued for 15 h at 20°
  3. filtrationThe precipitate was collected by filtration
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-373f8a98874c43eb921b97eb648f0fc1
Source dataset
uspto-grants-2003_06
Patent number
US06583133B1

Reaction notes

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