Thioglycolic Acid → HCID 20348735, compound

HRID 1730731Notes

Reaction equation

HRID 1730731 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 the 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-c0312fc46019469f96704e0805b62580
Source dataset
uspto-grants-1976_11
Patent number
US03993683

Reaction notes

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