Water → HCID 14514933, compound

HRID 1195318Notes

Reaction equation

HRID 1195318 reaction equation
Cl[CH2:2][C:3]1[C:11]([CH:12]([CH3:14])[CH3:13])=[CH:10][C:6]2[O:7][CH2:8][O:9][C:5]=2[CH:4]=1.[SH:15][CH2:16][C:17]([OH:19])=[O:18].[OH-].[Na+].O>C(O)C>[CH:12]([C:11]1[C:3]([CH2:2][S:15][CH2:16][C:17]([OH:19])=[O:18])=[CH:4][C:5]2[O:9][CH2:8][O:7][C:6]=2[CH:10]=1)([CH3:14])[CH3:13]

Participants

6

Reactant 4

HCID 962WaterHCID 1133Thioglycolic AcidHCID 14798Sodium HydroxideHCID 19001630HCID 19001630, compound

Product 1

HCID 14514933HCID 14514933, compoundYield 58.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A suspension of 3.3 g of 5-chloromethyl-6-isopropyl-1,3-benzodioxole (crude oil) in 10 ml of ethanol was added to a liquid mixture comprising 2.1 g of mercaptoacetic acid, 3 g of sodium hydroxide, 25 ml of ethanol and 25 ml of water to carry out the reaction at 80° C. for 40 minutes. The reaction mixture was concentrated, followed by the addition of water. The obtained mixture was washed with ethyl acetate. Concentrated hydrochloric acid was added to the mixture to acidify the aqueous layer, followed by the extraction with chloroform. The extract was washed with water, dried over anhydrous magnesium sulfate and filtered. The filtrate was distilled to remove the solvent. The residue was purified by column chromatography to obtain 2.45 g of the title compound as a colorless prismatic crystal.

Workup

  1. additionwas added to a liquid mixture
  2. customthe reaction at 80° C. for 40 minutes
  3. concentrationThe reaction mixture was concentrated
  4. additionfollowed by the addition of water
  5. washThe obtained mixture was washed with ethyl acetate
  6. additionConcentrated hydrochloric acid was added to the mixture
  7. extractionfollowed by the extraction with chloroform
  8. washThe extract was washed with water
  9. dry with materialdried over anhydrous magnesium sulfate
  10. filtrationfiltered
  11. distillationThe filtrate was distilled
  12. customto remove the solvent
  13. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-72fa4d04dea04094b0de10a8c94cc40c
Source dataset
uspto-grants-1992_05
Patent number
US05110956

Reaction notes

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