반응 #165477

반응 방정식

citric acid

methyl 3-methoxy-2-naphthoate

water

NaOH

→

3-methoxy-2-naphthoic acid

수율 92.0%

용매

MeOH

반응 조건

후처리

1. 1
   온도The mixture was heated at the reflux temp
2. 2
   온도cooled to room temp.
3. 3
   추출The resulting solution was extracted with EtOAc (2×100 mL)
4. 4
   세척The combined organic layers were washed with a saturated NaCl solution
5. 5
   건조dried (MgSO4)
6. 6
   농축concentrated under reduced pressure
7. 7
   기타The residue was triturated with hexane
8. 8
   세척then washed several times with hexane

실험 절차

A solution of methyl 3-methoxy-2-naphthoate (6.28 g, 29.10 mmol) and water (10 mL) in MeOH (100 mL) at room temp. was treated with a 1 N NaOH solution (33.4 mL, 33.4 mmol). The mixture was heated at the reflux temp. for 3 h, cooled to room temp., and made acidic with a 10% citric acid solution. The resulting solution was extracted with EtOAc (2×100 mL). The combined organic layers were washed with a saturated NaCl solution, dried (MgSO4) and concentrated under reduced pressure. The residue was triturated with hexane then washed several times with hexane to give 3-methoxy-2-naphthoic acid as a white solid (5.40 g, 92%): 1H-NMR (DMSO-d6) δ 3.88 (s, 3H), 7.34-7.41 (m, 2H), 7.49-7.54 (m, 1H), 7.83 (d, J=8.09 Hz, 1H), 7.91 (d, J=8.09 Hz, 1H), 8.19 (s, 1H), 12.83 (br s, 1H).

출처