Hydrochloric Acid → HCID 178490206, compound

HRID 424352

Reaction equation

HRID 424352 reaction equation
[OH-:1].[Na+].[CH2:3]([SH:7])[C:4](O)=O.[CH3:8][O:9][C:10]1[CH:17]=[CH:16][C:13]([CH2:14]Cl)=[CH:12][C:11]=1[N+:18]([O-:20])=[O:19].Cl>CO>[CH3:8][O:9][C:10]1[CH:17]=[CH:16][C:13]([CH2:14][CH2:4][C:3]([OH:1])=[S:7])=[CH:12][C:11]=1[N+:18]([O-:20])=[O:19]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1133Thioglycolic AcidHCID 14798Sodium HydroxideHCID 807854-(Chloromethyl)-2-nitroanisole

Product 1

HCID 178490206HCID 178490206, compoundYield 103.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a cold solution of sodium hydroxide (9.75 g, 240 mmol) in methanol (200 mL), was added thioglycollic acid (11.25 g, 120 mmol) slowly over 30 min. Sodium thioglycollate precipitated and was redissolved by stirring and warming the mixture. The sodium thioglycollate solution was then cooled to room temperature and 4-methoxy-3-nitrobenzyl chloride (30.0 g, 120 mmol) was added in portions to reduce the intensity of exothermic reaction. The resulting mixture was heated to reflux temperature and maintained at reflux temperature for 4 h. The heated mixture was then cooled and poured onto crushed ice (1 kg) containing hydrochloric acid (50 mL). A precipitate formed. The precipitate was separated by filtration, washed with ice cold water and dried under vacuum to yield 30 g (95% yield) of the desired 4-methoxy-3-nitrobenzylthioacetic acid product. m.p. 130-132° C.

Workup

  1. customSodium thioglycollate precipitated
  2. dissolutionwas redissolved
  3. temperaturewarming the mixture
  4. customthe intensity of exothermic reaction
  5. temperatureThe resulting mixture was heated
  6. temperatureto reflux temperature
  7. temperaturemaintained
  8. temperatureat reflux temperature for 4 h
  9. temperatureThe heated mixture was then cooled
  10. additionpoured
  11. customA precipitate formed
  12. customThe precipitate was separated by filtration
  13. washwashed with ice cold water
  14. customdried under vacuum

Sources & evidence

ORD record
ord-bf0401ec1ff24fe39ccaf024f80df387
Source dataset
uspto-grants-2012_01
Patent number
US08106033B2

Linked notes

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