tert-Butanol → tert-Butyl (4-methylphenyl)acetate

HRID 25152

Reaktionsgleichung

Reaktionsgleichung von HRID 25152
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=[O:10])=[CH:4][CH:3]=1.[C:12](O)([CH3:15])([CH3:14])[CH3:13].C1(N=C=NC2CCCCC2)CCCCC1>CN(C1C=CN=CC=1)C.ClCCl>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])=[CH:6][CH:7]=1

Komponenten

6

Edukt 3

HCID 6386tert-ButanolHCID 10868DicyclohexylcarbodiimideHCID 248474p-Tolylacetic acid

Produkt 1

HCID 12362014tert-Butyl (4-methylphenyl)acetate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6344DichloromethaneLösungsmittel2×

Reaktionsbedingungen

Temperatur
25 °C

Versuchsvorschrift

450 g (3 mol) of 4-methylphenyl-acetic acid (Aldrich), 1.13 l (12 mol) of tert-butanol and 90 g (0.74 mol) of 4-(N,N-dimethylamino)pyridine are dissolved in 2 l of dichloromethane. After addition of 680 g (3.3 mol of dicyclohexylcarbodiimide, dissolved in 400 ml of dichloromethane, the mixture is stirred at 25° C. for 20 h, the precipitated urea is filtered off with suction and flashed with 200 ml of dichloromethane, and the organic phase is washed twice each with 500 ml of 2 M hydrochloric acid and water. The organic phase is concentrated and distilled.

Aufarbeitung

  1. filtrationthe precipitated urea is filtered off with suction
  2. washthe organic phase is washed twice each with 500 ml of 2 M hydrochloric acid and water
  3. concentrationThe organic phase is concentrated
  4. distillationdistilled

Quellen und Nachweise

ORD-Eintrag
ord-d11bec94770c4b5c9e1b124727c52863
Quelldatensatz
uspto-grants-2005_02
Patentnummer
US06858622B2

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