(4-Chlorophenyl)acetic acid → (4-Chlorophenyl)acetic acid tert-butyl ester

HRID 22932

Reaktionsgleichung

Reaktionsgleichung von HRID 22932
C([O:5][CH:6]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])N(C)C)(C)(C)C.[Cl:15][C:16]1[CH:21]=[CH:20][C:19]([CH2:22]C(O)=O)=[CH:18][CH:17]=1>C1(C)C=CC=CC=1.CCOC(C)=O>[C:11]([O:10][C:6](=[O:5])[CH2:22][C:19]1[CH:20]=[CH:21][C:16]([Cl:15])=[CH:17][CH:18]=1)([CH3:12])([CH3:13])[CH3:14]

Komponenten

5

Edukt 2

HCID 15880(4-Chlorophenyl)acetic acidHCID 5477121,1-bis(1,1-dimethylethoxy)-N,N,N-trimethylamine

Produkt 1

HCID 13380183(4-Chlorophenyl)acetic acid tert-butyl esterAusbeute 30,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1140TolueneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a suspension of N,N-dimethyl-formamide-di-tert-butyl acetal (25 ml, 104.4 mmol) in dry toluene (90 ml) was added p-chlorophenyl acetic acid (5.94 g, 34.8 mmol) and the whole heated at 80° C. for 1 h. The mixture was diluted with EtOAc (50 ml) and washed with water (50 ml), 3% aqueous NaHCO3 solution (50 ml) and brine (20 ml) and then dried over MgSO4 and evaporated to give an oil. This oil was purified using 35%, then 50% DCM in pentane to give the title product (2.4 g, 30%); 1HNMR (400 MHz, CDCl3) δ: 1.42 (s, 9H), 3.44 (s, 2H), 7.20 (d, 2H), 7.28 (d, 2H).

Aufarbeitung

  1. washwashed with water (50 ml), 3% aqueous NaHCO3 solution (50 ml) and brine (20 ml)
  2. dry with materialdried over MgSO4
  3. customevaporated
  4. customto give an oil
  5. customThis oil was purified

Quellen und Nachweise

ORD-Eintrag
ord-701d47aedcc34c7e947611658d0fc50a
Quelldatensatz
uspto-grants-2005_02
Patentnummer
US06849649B2

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