反応 #1605771

反応方程式

2-hydroxy-4-methylbenzoic acid

K2CO3

KOH

HCl

→

2-methoxy-4-methylbenzoic acid

溶媒

acetone

MeOH

反応条件

後処理

1. 1
   温度the reaction mixture heated
2. 2
   温度at reflux for 48 hrs
3. 3
   ろ過was filtered
4. 4
   その他the filtrate was evaporated
5. 5
   その他to give the crude methyl 2-methoxy-4-methylbenzoate
6. 6
   温度the solution heated
7. 7
   温度at reflux 48 hrs
8. 8
   温度After cooling the reaction mixture
9. 9
   抽出extracted with ethyl acteate
10. 10
    洗浄The organic layer was washed with brine
11. 11
    乾燥dried over MgSO4
12. 12
    ろ過filtered
13. 13
    その他evaporated
14. 14
    その他The residue was triturated with Ethyl acetate/Hexane

実験手順

To a solution of 2-hydroxy-4-methylbenzoic acid (25 g, 0.164 mol) in acetone (350 mL) was added K2CO3 (68 g, 0.492 mmol) followed by MeI (41 mL, 0.656 mmol) and the reaction mixture heated at reflux for 48 hrs. After cooling to r.t. the reaction mixture was filtered and the filtrate was evaporated to give the crude methyl 2-methoxy-4-methylbenzoate. KOH (11.3 g, 1.2 eq) was dissolved in MeOH (300 mL) and the crude ester was added to the mixture and the solution heated at reflux 48 hrs. After cooling the reaction mixture was acidified with aq. HCl (1N) and extracted with ethyl acteate. The organic layer was washed with brine, dried over MgSO4, filtered and evaporated. The residue was triturated with Ethyl acetate/Hexane to give 20 g of 2-methoxy-4-methylbenzoic acid as a cream white solid (85% yield)

出典