1,2-Dichloroethane → 2-Chloro-4-methoxyphenylacetic acid ethylester

HRID 1095861Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1095861
[CH2:1]([OH:3])[CH3:2].C(Cl)CCl.C(N(CC)CC)C.[Cl:15][C:16]1[CH:21]=[C:20]([O:22][CH3:23])[CH:19]=[CH:18][C:17]=1[CH2:24][C:25](O)=[O:26]>CN(C1C=CN=CC=1)C.C(Cl)Cl>[CH2:1]([O:3][C:25](=[O:26])[CH2:24][C:17]1[CH:18]=[CH:19][C:20]([O:22][CH3:23])=[CH:21][C:16]=1[Cl:15])[CH3:2]

Komponenten

7

Edukt 4

HCID 111,2-DichloroethaneHCID 702EthanolHCID 8471TriethylamineHCID 42091322-(2-Chloro-4-methoxyphenyl)acetic acid

Produkt 1

HCID 573835082-Chloro-4-methoxyphenylacetic acid ethylesterAusbeute 64 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

Ethanol (8.72 mL, 150 mmol), DMAP (304 mg, 2 mmol), EDC (9.56 g, 50 mmol), and triethylamine (6.91 mL, 50 mmol) were added under cooling (ice) to a solution of (2-chloro-4-methoxy-phenyl)-acetic acid (10.00 g, 50 mmol, [CAS Reg. No. 91367-09-8]) in CH2Cl2 (200 mL). The reaction mixture was stirred at r.t. overnight, then diluted (CH2Cl2), and washed (1N HCl). The organic layer was dried (Na2SO4), and the solvent was evaporated. Purification of the residue by column chromatography (silica gel, heptane:ethyl acetate=100:0-70:30) gave the title compound (7.27 g, 64%). 1H NMR (300 MHz, CDCl3) δ 7.18 (1H, d), 6.94 (1H, d), 6.79 (1H, dd), 4.17 (2H, q), 3.79 (3H, s), 3.69 (2H, s), 1.26 (3H, t).

Aufarbeitung

  1. washwashed (1N HCl)
  2. dry with materialThe organic layer was dried (Na2SO4)
  3. customthe solvent was evaporated
  4. customPurification of the residue by column chromatography (silica gel, heptane:ethyl acetate=100:0-70:30)

Quellen und Nachweise

ORD-Eintrag
ord-9b8dc8a50fb54aba9834a80cec6cd526
Quelldatensatz
uspto-grants-2012_03
Patentnummer
US08138189B2

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