Réaction #52064

Équation de réaction

tert-butyl bromoacetate

3-hydroxybenzaldehyde

potassium tert-butoxide

tert-butanol

→

title compound

Rendement 36.5%

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

Rendement 36.5%

Solvants

DMF

Conditions de réaction

Traitement

1. 1
   workup.STIRRINGThe reaction was stirred for 1 hour
2. 2
   Autrewas quenched with 200 mL of water
3. 3
   ExtractionThe product was extracted into EtOAc
4. 4
   Lavagethe organic solution was washed with water
5. 5
   Séchagedried over MgSO4
6. 6
   Filtrationfiltered
7. 7
   Concentrationconcentrated in vacuo
8. 8
   AutrePurification via flash chromatography on silica gel (9:1 hexanes:EtOAc)

Mode opératoire

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).

Source