Thioglycolic Acid → 2-(Tritylthio)acetic acid

HRID 359130

Reaction equation

HRID 359130 reaction equation
[C:1]1([C:7]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[SH:21][CH2:22][C:23]([OH:25])=[O:24]>FC(F)(F)C(O)=O>[C:7]([S:21][CH2:22][C:23]([OH:25])=[O:24])([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 1133Thioglycolic AcidHCID 6457Triphenylcarbinol

Product 1

HCID 42453062-(Tritylthio)acetic acidYield 94.4%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

This compound was synthesized by the condensation of triphenylmethanol (2.84 g, 10.8 mmoles) with mercaptoacetic acid (0.75 ml, 10.8 mmoles) in 19 ml trifluoracetic acid. The TFA was removed in vacuo, giving an orange oil, which was purified by dissolution in ether and extraction with 1 N NaOH. The aqueous phase was acidified with 6N HCl, and extracted with two 30 ml portions of ether. The ethereal phase was dried over MgSO4 and evaporated to give 3.41 g (93%) of a white solid.

Workup

  1. customThe TFA was removed in vacuo
  2. customgiving an orange oil, which
  3. customwas purified by dissolution in ether
  4. extractionextraction with 1 N NaOH
  5. extractionextracted with two 30 ml portions of ether
  6. dry with materialThe ethereal phase was dried over MgSO4
  7. customevaporated

Sources & evidence

ORD record
ord-3491d70d6f84495783e0f1a510576c8c
Source dataset
uspto-grants-1991_03
Patent number
US04999424

Linked notes

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