Methyl iodide → Methyl 3-methoxy-4-methyl-2-nitrobenzoate

HRID 1672478

반응식

HRID 1672478 반응식
O[C:2]1[C:3]([N+:12]([O-:14])=[O:13])=[C:4]([CH:8]=[CH:9][C:10]=1[CH3:11])[C:5]([OH:7])=[O:6].[C:15]([O-])([O-])=O.[K+].[K+].CI.C(Cl)Cl.[CH3:26][OH:27]>CN(C=O)C.O>[CH3:26][O:27][C:2]1[C:3]([N+:12]([O-:14])=[O:13])=[C:4]([CH:8]=[CH:9][C:10]=1[CH3:11])[C:5]([O:7][CH3:15])=[O:6]

참가 물질

7

반응물 4

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 813743-Hydroxy-4-methyl-2-nitrobenzoic acidHCID 21226129Dichloromethane methanol

생성물 1

HCID 14543060Methyl 3-methoxy-4-methyl-2-nitrobenzoate수율 94.7%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

To a solution of 3-hydroxy-4-methyl-2-nitrobenzoic acid (365 g, 1.85 mol) in DMF (3280 mL) were added K2CO3 (524.4 g, 3.80 mol) and MeI (788 g, 5.55 mol) in one portion. Then the reaction mixture was stirred at room temperature overnight. TLC(CH2Cl2/MeOH=3:1) indicated the reaction was complete. Water (9 L) was added to the reaction mixture and the mixture was extracted with EtOAc (3 L×2). The combined organic layers were washed with 1 N aq. NaOH (1 L×2) and brine, dried over anhydrous Na2SO4 and concentrated in vacuo to give the title compound (395 g, 94.7%) as a light yellow solid.

후처리

  1. extractionthe mixture was extracted with EtOAc (3 L×2)
  2. washThe combined organic layers were washed with 1 N aq. NaOH (1 L×2) and brine
  3. dry with materialdried over anhydrous Na2SO4
  4. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-bc9a8d433be54c0487e702831b7e51a7
출처 데이터셋
uspto-grants-2011_08
특허 번호
US07998978B2

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