Sulfuric Acid → 3-Hydroxy-4-(methoxycarbonyl)benzoic acid

HRID 1881541노트

반응식

HRID 1881541 반응식
N[C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[C:11]([O:13][CH3:14])=[O:12])[C:5]([OH:7])=[O:6].N([O-])=[O:16].[Na+].S(=O)(=O)(O)O>Cl.C(O)(=O)C>[OH:16][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[C:11]([O:13][CH3:14])=[O:12])[C:5]([OH:7])=[O:6]

참가 물질

6

반응물 3

HCID 1118Sulfuric AcidHCID 52355003-Amino-4-(methoxycarbonyl)benzoic acidHCID 23668193Sodium Nitrite

생성물 1

HCID 670501783-Hydroxy-4-(methoxycarbonyl)benzoic acid수율 53%

시약·촉매·용매 2

HCID 176Acetic Acid용매HCID 313Hydrochloric Acid용매

실험 절차

To 3-amino-4-methoxycarbonylbenzoic acid (1.95 g, 10 mmol) suspended in 3 M hydrochloric acid (12.5 mL) and acetic acid (20 mL), an aqueous solution (20 mL) of sodium nitrite (0.69 g, 10 mmol) was added at −10° C., and the resulting solution was stirred for 30 minutes. The solution was added to 10% aqueous sulfuric acid (30 mL) at 0° C., and the resulting reaction mixture was heated with reflux for 1 hour. The desired product was extracted with ethyl acetate, and the extract was dried over magnesium sulfate and purified by silica gel column chromatography to give 1.04 g of the desired product as a white solid (yield 53%).

후처리

  1. customthe resulting reaction mixture
  2. temperaturewas heated
  3. temperaturewith reflux for 1 hour
  4. extractionThe desired product was extracted with ethyl acetate
  5. dry with materialthe extract was dried over magnesium sulfate
  6. custompurified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-72c77d7a66544600b52f427bdaadd3e7
출처 데이터셋
uspto-grants-2012_11
특허 번호
US08318796B2

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