Oxalyl chloride → (2R)-2-(2,4-Di-t-butylphenyloxy)propanoyl chloride

HRID 248196Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 248196
[C:1]([C:5]1[CH:10]=[C:9]([C:11]([CH3:14])([CH3:13])[CH3:12])[CH:8]=[CH:7][C:6]=1[O:15][C@H:16]([CH3:20])[C:17](O)=[O:18])([CH3:4])([CH3:3])[CH3:2].C(Cl)(=O)C([Cl:24])=O>CN(C)C=O.C(Cl)Cl>[C:1]([C:5]1[CH:10]=[C:9]([C:11]([CH3:14])([CH3:13])[CH3:12])[CH:8]=[CH:7][C:6]=1[O:15][C@H:16]([CH3:20])[C:17]([Cl:24])=[O:18])([CH3:4])([CH3:3])[CH3:2]

Komponenten

5

Edukt 2

HCID 65578Oxalyl chlorideHCID 18651686(2R)-2-(2,4-Di-t-butylphenyloxy)propanoic Acid

Produkt 1

HCID 53944384(2R)-2-(2,4-Di-t-butylphenyloxy)propanoyl chlorideAusbeute 99 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideKatalysatorHCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a mixture of 675 m9 (2.2 mmol) of (2R)-2-(2,4-di-t-butylphenyloxy)propanoic acid (18) and 4 drops of N,N-dimethylformamide in methylene chloride (20 mL) at 0° C. under a nitrogen atmophere was added 1.21 mL (2.4 mmol) of a 2M solution of oxalyl chloride in methylene chloride dropwise over a 10 min period. The reaction mixture was allowed to stir at room temperature overnight. The solvent and any excess oxalyl chloride was removed by rotary evaporation and dried (under vacuum) to afford 715 mg (99%) of (2R)-2-(2,4-di-t-butylphenyloxy)propanoyl chloride (16) as a crude yellow liquid: 1H NMR (CDCl3) δ1.29 (s, 9 H), 1.42 (s, 9 H), 1.76-1.79 (d, 3 H), 4.94-5.00 (q, 1 H), 6.50-6.(d, 1 H), 7.12-7.16 (d, 1 H), 7.36 (s, 1 H); 13C NMR (CDCl3) δ175.0, 152.8, 144.1, 137.4, 124.6, 123.4, 110.6, 78.6, 35.1, 34.3, 1.5, 30.0, 18.0.

Aufarbeitung

  1. customThe solvent and any excess oxalyl chloride was removed by rotary evaporation
  2. customdried (under vacuum)

Quellen und Nachweise

ORD-Eintrag
ord-8c9e0cd55d904bcbb902ea44eb609e28
Quelldatensatz
uspto-grants-1993_05
Patentnummer
US05208345

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