Nitric Acid → Methyl 3-hydroxy-4-methoxy-2-nitrobenzoate

HRID 1095782노트

반응식

HRID 1095782 반응식
[N+:1]([O-:4])(O)=[O:2].[OH:5][C:6]1[CH:7]=[C:8]([CH:13]=[CH:14][C:15]=1[O:16][CH3:17])[C:9]([O:11][CH3:12])=[O:10]>C(O)(=O)C>[OH:5][C:6]1[C:7]([N+:1]([O-:4])=[O:2])=[C:8]([CH:13]=[CH:14][C:15]=1[O:16][CH3:17])[C:9]([O:11][CH3:12])=[O:10]

참가 물질

4

반응물 2

HCID 944Nitric AcidHCID 4056967Methyl 3-hydroxy-4-methoxybenzoate

생성물 1

HCID 59268115Methyl 3-hydroxy-4-methoxy-2-nitrobenzoate수율 27.4%

시약·촉매·용매 1

HCID 176Acetic Acid용매

실험 절차

Nitric acid (95%, 42 g, 0.62 mol) was added dropwise (internal temperature kept below 5° C.) to a solution of methyl 3-hydroxy-4-methoxybenzoate (96.5%, 100 g, 0.53 mol) and acetic acid (250 mL) at 0° C. After 10 min at 0° C., a large amount of precipitate had formed and was collected by filtration. The filter cake was washed with water (100 mL×2), and then the crude product was recrystallized from methanol (40 mL) to give 33 g of methyl 3-hydroxy-4-methoxy-2-nitrobenzoate as a light yellow solid. 1H NMR (400 MHz, DMSO-d6): δ 10.64 (s, 1H), 7.49 (d, 1H), 7.22 (d, 1H), 3.93 (s, 3H), 3.76 (s, 3H); MS (ESI): 227.9.

후처리

  1. customa large amount of precipitate had formed
  2. filtrationwas collected by filtration
  3. washThe filter cake was washed with water (100 mL×2)
  4. customthe crude product was recrystallized from methanol (40 mL)

출처 및 근거

ORD 기록
ord-14b9d4e8b664451992dc8426c75e6c6d
출처 데이터셋
uspto-grants-2012_03
특허 번호
US08138205B2

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