Reaktion #52064

Reaktionsgleichung

tert-butyl bromoacetate

3-hydroxybenzaldehyde

potassium tert-butoxide

tert-butanol

→

title compound

Ausbeute 36.5%

(3-Formyl-phenoxy)-acetic acid tert-butyl ester

Ausbeute 36.5%

Lösungsmittel

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGThe reaction was stirred for 1 hour
2. 2
   Sonstigewas quenched with 200 mL of water
3. 3
   ExtraktionThe product was extracted into EtOAc
4. 4
   Waschenthe organic solution was washed with water
5. 5
   Trocknendried over MgSO4
6. 6
   Filtrationfiltered
7. 7
   Einengenconcentrated in vacuo
8. 8
   SonstigePurification via flash chromatography on silica gel (9:1 hexanes:EtOAc)

Vorschrift

To a solution of 3-hydroxybenzaldehyde (5.00 g, 40.9 mmol) in DMF (40 mL) was added 1M potassium tert-butoxide in tert-butanol (40.9 mL, 40.9 mmol). The reaction was stirred for 2 minutes and tert-butyl bromoacetate (6.61 mL, 40.9 mmol) was added. The reaction was stirred for 1 hour and was quenched with 200 mL of water. The product was extracted into EtOAc and the organic solution was washed with water, dried over MgSO4, filtered and concentrated in vacuo. Purification via flash chromatography on silica gel (9:1 hexanes:EtOAc) afforded the title compound as a clear oil (3.53 g). 1H NMR (400 MHz, CDCl3) δ 9.94 (s, 1H), 7.48 (m, 2H), 7.32 (s, 1H), 7.21 (m, 1H), 4.56 (s, 2H), 1.45 (s, 9H).

Quelle