Diethyl Ether → Methyl 5-chloro-2-formylbenzoate

HRID 2170754Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2170754
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH:11]=[O:12])=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8].[C:13]([O-])([O-])=O.[K+].[K+].CI.CCOCC>CN(C=O)C>[CH3:13][O:8][C:7](=[O:9])[C:6]1[CH:10]=[C:2]([Cl:1])[CH:3]=[CH:4][C:5]=1[CH:11]=[O:12]

Komponenten

6

Edukt 4

HCID 3283Diethyl EtherHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 71762095-Chloro-2-formylbenzoic acid

Produkt 1

HCID 58437623Methyl 5-chloro-2-formylbenzoateAusbeute 65 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a heterogeneous mixture of 5-chloro-2-formyl-benzoic acid (1.0 g, 5.42 mmol) and K2CO3 (1.12 g, 8.13 mmol) in DMF (7 ml) was added MeI (0.41 ml, 6.5 mmol) at RT. The reaction mixture was stirred for 4 h then diluted into Et2O and washed with water (2×). The organic layer was dried over Na2SO4, filtered and evaporated to dryness to yield the crude title compound (700 mg, 3.52 mmol, 65%) as a light yellow solid, which was used without further purification. HPLC: AtRet=1.84 min; LC-MS: m/z 199.3 [M+H]+; 1H NMR (400 MHz, DMSO-d6): 3.91 (s, 3H), 7.84-7.94 (m, 3H), 10.33 (s, 1H).

Aufarbeitung

  1. washwashed with water (2×)
  2. dry with materialThe organic layer was dried over Na2SO4
  3. filtrationfiltered
  4. customevaporated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-4a65d71363bf4d9e95332fd8d83d18cd
Quelldatensatz
uspto-grants-2015_06
Patentnummer
US09051279B2

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