Реакция #1605771

Уравнение реакции

2-hydroxy-4-methylbenzoic acid

K2CO3

KOH

HCl

→

2-methoxy-4-methylbenzoic acid

Растворители

acetone

MeOH

Условия реакции

Обработка

1. 1
   Температураthe reaction mixture heated
2. 2
   Температураat reflux for 48 hrs
3. 3
   Фильтрацияwas filtered
4. 4
   Другоеthe filtrate was evaporated
5. 5
   Другоеto give the crude methyl 2-methoxy-4-methylbenzoate
6. 6
   Температураthe solution heated
7. 7
   Температураat reflux 48 hrs
8. 8
   ТемператураAfter cooling the reaction mixture
9. 9
   Экстракцияextracted with ethyl acteate
10. 10
    ПромывкаThe organic layer was washed with brine
11. 11
    Сушкаdried over MgSO4
12. 12
    Фильтрацияfiltered
13. 13
    Другоеevaporated
14. 14
    ДругоеThe residue was triturated with Ethyl acetate/Hexane

Методика

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)

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