Thioglycolic Acid → HCID 20348735, compound

HRID 1701155Notes

Reaction equation

HRID 1701155 reaction equation
[SH:1][CH2:2][C:3]([OH:5])=[O:4].[OH-].[K+].[F:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[C:15]1[CH:20]=[CH:19][C:18]([CH:21](Cl)[CH3:22])=[CH:17][CH:16]=1.C1(C)C=CC=CC=1>CO.O>[F:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[C:15]1[CH:16]=[CH:17][C:18]([CH:21]([S:1][CH2:2][C:3]([OH:5])=[O:4])[CH3:22])=[CH:19][CH:20]=1

Participants

7

Reactant 4

HCID 1133Thioglycolic AcidHCID 1140TolueneHCID 14797Potassium HydroxideHCID 203487834'-(1-Chloroethyl)-2-fluoro-1,1'-biphenyl

Product 1

HCID 20348735HCID 20348735, compoundYield 55%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

6.35 gm (0.055 mol) of 80% mercaptoacetic acid were admixed in 70 ml of methanol with a solution of 6.2 gm (0.11 mol) of potassium hydroxide in 6.2 ml of water. To the solution of dipotassium salt, 11.7 gm (0.05 mol) of 1-(2'-fluoro-4-biphenylyl)-1-chloro-ethane were added, the reaction mixture was rinsed with 20 ml of methanol and stirred for 18 hours at room temperature. Subsequently, the mixture was evaporated, the residue was digested with acetone, and the precipitated potassium salt was suction-filtered off. The free acid was obtained by dissolving the salt in water and acidifying the solution. M.p 128°-130° C. (from toluene). Yield: 55% of theory.

Workup

  1. washthe reaction mixture was rinsed with 20 ml of methanol
  2. customSubsequently, the mixture was evaporated
  3. filtrationthe precipitated potassium salt was suction-filtered off
  4. customThe free acid was obtained

Sources & evidence

ORD record
ord-84eb262934c24fdab5d2cb07f93fb5d2
Source dataset
uspto-grants-1980_03
Patent number
US04191776

Reaction notes

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