Hydrochloric Acid → HCID 178490206, Verbindung

HRID 1183214Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1183214
[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]

Komponenten

6

Edukt 4

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

Produkt 1

HCID 178490206HCID 178490206, VerbindungAusbeute 103,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-d9cbe00fcb694e36b0a0b63ae35f9cb3
Quelldatensatz
uspto-grants-2014_03
Patentnummer
US08664272B2

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