Reaktion #80200

Reaktionsgleichung

diethyl azodicarboxylate

methyl 3-methoxysalicylate

benzyl alcohol

triphenylphosphine

→

title compound

Ausbeute 58.2%

2-Benzyloxy-3-methoxybenzoic acid methyl ester

Ausbeute 58.2%

Lösungsmittel

ethyl acetate

tetrahydrofuran

dimethylformamide

Reaktionsbedingungen

Aufarbeitung

1. 1
   Waschenthe resulting solution was washed sequentially with water and brine
2. 2
   TrocknenThe ethyl acetate solution was dried over anhydrous sodium sulfate
3. 3
   Einengenconcentrated to dryness in vacuo
4. 4
   SonstigeThe residue was triturated with diethyl ether
5. 5
   Filtrationfiltered
6. 6
   Sonstigeto remove triphenylphosphine oxide
7. 7
   EinengenThe ether solution was concentrated to dryness in vacuo
8. 8
   Sonstigethe residue was purified by column chromatography on silica gel
9. 9
   Wascheneluting with 95:5 hexane/ethyl acetate

Vorschrift

To a solution of methyl 3-methoxysalicylate (1.0 g, 5.49 mmol) in 5 ml tetrahydrofuran and 5 ml dimethylformamide was added sequentially at room temperature, benzyl alcohol (0.71 ml, 6.86 mmol), triphenylphosphine (2.16 g, 8.23 mmol) and diethyl azodicarboxylate (1.3 ml, 8.23 mmol). The reaction solution was stirred at room temperature overnight, then ethyl acetate was added and the resulting solution was washed sequentially with water and brine. The ethyl acetate solution was dried over anhydrous sodium sulfate and concentrated to dryness in vacuo. The residue was triturated with diethyl ether and filtered to remove triphenylphosphine oxide. The ether solution was concentrated to dryness in vacuo and the residue was purified by column chromatography on silica gel, eluting with 95:5 hexane/ethyl acetate, yielding the title compound as an oil (870 mg 58% yield).

Quelle