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Glyoxylic Acid → 4-tert-Butyl-2,6-dimethylmandelic acid acetate

HRID 1183850
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1183850
[C:1]([OH:5])(=[O:4])[CH:2]=[O:3].[C:6]([C:10]1[CH:15]=[C:14]([CH3:16])[CH:13]=[C:12]([CH3:17])[CH:11]=1)([CH3:9])([CH3:8])[CH3:7].S(=O)(=O)(O)O>C(O)(=O)C>[C:1]([OH:5])(=[O:4])[CH3:2].[C:6]([C:10]1[CH:11]=[C:12]([CH3:17])[C:13]([CH:2]([OH:3])[C:1]([OH:5])=[O:4])=[C:14]([CH3:16])[CH:15]=1)([CH3:9])([CH3:8])[CH3:7]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 760Glyoxylic AcidHCID 1118Sulfuric AcidHCID 73785-Tert-butyl-m-xylene

Produkt 1

HCID 674987574-tert-Butyl-2,6-dimethylmandelic acid acetate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Reaktionsbedingungen

Temperatur
35 °C

Versuchsvorschrift

A mixture of 89 g of 50% aqueous glyoxylic acid solution [0.6 mol], 400 ml of glacial acetic acid and 81.1 g [0.5 mol] of 1-tert-butyl-3,5-dimethylbenzene is initially charged. Starting at room temperature, 85.8 g of 96% strength sulfuric acid [0.84 mol] are added dropwise over a period of 15 minutes, during which time the temperature of the reaction mixture increases to about 35° C. The mixture is heated to 60° C. and stirred at this temperature for 9 hours. The cooled reaction mixture is then stirred into 750 ml of ice-water. The mixture is extracted three times with in each case 150 ml of methylene chloride, the combined organic phases are washed with 100 ml of saturated aqueous NaCl solution, dried over sodium sulfate and concentrated under reduced pressure. This gives 136.7 g of a yellowish thick oil, which, according to GC/MS(sil.), has the following composition:

Aufarbeitung

  1. additionis initially charged
  2. customStarting at room temperature
  3. temperatureThe mixture is heated to 60° C.
  4. customThe cooled reaction mixture
  5. extractionThe mixture is extracted three times with in each case 150 ml of methylene chloride
  6. washthe combined organic phases are washed with 100 ml of saturated aqueous NaCl solution
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-81dc4426910f4a7eac76177a65fbde51
Quelldatensatz
uspto-grants-2014_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08664428B2

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