Trityl chloride → 3-Triphenylmethylthio-2-methylpropanoic acid

HRID 2419446Notes

Reaction equation

HRID 2419446 reaction equation
[SH:1][CH2:2][CH:3]([CH3:7])[C:4]([OH:6])=[O:5].[C:8](Cl)([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)([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(Cl)Cl>[C:9]1([C:8]([C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)([C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[S:1][CH2:2][CH:3]([CH3:7])[C:4]([OH:6])=[O:5])[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

4

Reactant 2

HCID 6456Trityl chlorideHCID 1529103-Mercaptoisobutyric acid

Product 1

HCID 213191543-Triphenylmethylthio-2-methylpropanoic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 3-mercapto-2-methylpropanoic acid (1.2 g.) and tritylchloride (2.9 g.) in methylene chloride (50 ml.) is kept at room temperature for 2 hours. The mixture is warmed in a steam bath for 20 minutes and then evaporated to dryness in vacuo and the residue is dissolved in saturated aqueous sodium bicarbonate and the solution is washed with ethyl acetate. The aqueous phase is acidified to pH 3 and extracted with ethyl acetate. The organic layer is dried and concentrated to dryness to give 3-triphenylmethylthio-2-methylpropanoic acid. Rf 0.8 (Silica gel, Benzene/acetic acid 3:1).

Workup

  1. temperatureThe mixture is warmed in a steam bath for 20 minutes
  2. customevaporated to dryness in vacuo
  3. dissolutionthe residue is dissolved in saturated aqueous sodium bicarbonate
  4. washthe solution is washed with ethyl acetate
  5. extractionextracted with ethyl acetate
  6. customThe organic layer is dried
  7. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-55c465f387d44d09ad5256a5226f7a73
Source dataset
uspto-grants-1978_08
Patent number
US04105776

Reaction notes

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