Water → HCID 10315203, compound

HRID 2253981Notes

Reaction equation

HRID 2253981 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([S:9][CH2:10][C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH:5]=[CH:6][C:7]=1[OH:8].N1[CH:23]=[CH:22]C=CC=1.[C:24](Cl)(=[O:26])[CH3:25].[OH2:28]>C(Cl)Cl>[C:24]([O:1][C:2]1[CH:3]=[C:4]([S:9][CH2:10][C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH:5]=[CH:6][C:7]=1[O:8][C:22](=[O:28])[CH3:23])(=[O:26])[CH3:25]

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 6367Acetyl chlorideHCID 10422547HCID 10422547, compound

Product 1

HCID 10315203HCID 10315203, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

After 17.7 g of tert-butyl (3,4-dihydroxyphenylthio)acetate was dissolved in 70 ml of methylene chloride, 11.4 ml of pyridine and then 10.0 ml of acetyl chloride were added to the solution under ice cooling. After stirring for 20 minutes, water was added and the resulting mixture was extracted twice with methylene chloride. After drying over magnesium sulfate, the solvent was distilled off to give the crude product. The crude product was subjected to silica gel column chromatography and the column was eluted with hexane-ethyl acetate to give 19.7 g of tert-butyl (3,4-diacetoxyphenylthio)acetate.

Workup

  1. extractionthe resulting mixture was extracted twice with methylene chloride
  2. dry with materialAfter drying over magnesium sulfate
  3. distillationthe solvent was distilled off
  4. customto give the crude product
  5. washthe column was eluted with hexane-ethyl acetate

Sources & evidence

ORD record
ord-2e8c8a877e3d45bfa98178ac7c29a224
Source dataset
uspto-grants-1993_08
Patent number
US05233035

Reaction notes

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