Sodium Hydroxide → 3-Ethoxy-6-hydroxy-2-methylbenzoic acid

HRID 577549노트

반응식

HRID 577549 반응식
Br[C:2]1[C:7]([C:8]([O:10]C)=[O:9])=[C:6]([CH3:12])[C:5]([O:13][CH2:14][CH3:15])=[CH:4][CH:3]=1.[OH-].[Na+].C(=O)(O)[O-:19].[Na+].CN[C@@H]1CCCC[C@H]1NC>CS(C)=O.O.S([O-])([O-])(=O)=O.[Cu+2].C(OCC)(=O)C>[CH2:14]([O:13][C:5]1[C:6]([CH3:12])=[C:7]([C:2]([OH:19])=[CH:3][CH:4]=1)[C:8]([OH:10])=[O:9])[CH3:15]

참가 물질

9

반응물 4

HCID 14798Sodium HydroxideHCID 516892Sodium BicarbonateHCID 2733821trans-N,N'-dimethyl-1,2-cyclohexanediamineHCID 86723776Methyl 6-bromo-3-ethoxy-2-methylbenzoate

생성물 1

HCID 867237773-Ethoxy-6-hydroxy-2-methylbenzoic acid수율 79%

시약·촉매·용매 4

HCID 24462Copper Sulfate촉매HCID 679Dimethyl Sulfoxide용매HCID 962Water용매2회HCID 8857Ethyl Acetate용매

반응 조건

온도
95 °C

실험 절차

A solution of methyl 6-bromo-3-ethoxy-2-methylbenzoate (114c, 0.298 g, 1.09 mmol) in DMSO (4 mL) was treated with 10M NaOH (1.0 mL, 10 mmol) and heated at 95° C. After 1 hour, the ester was hydrolyzed. The reaction mixture was cooled to room temperature and sodium bicarbonate (0.850 g, 10.1 mmol) and water (3 mL) were added. The suspension was sonicated until homogeneous. A solution of copper(II) sulfate (0.0348 g, 0.218 mmol) and trans-N,N′-dimethylcyclohexane-1,2-diamine (0.071 mL, 0.44 mmol) in water (2.0 mL) was added. The reaction mixture was heated at 95° C. for 1 hour. The reaction mixture was cooled to room temperature, poured into ethyl acetate, and washed with 1N HCl and brine. The organic layer was dried over Na2SO4 and concentrated under vacuum to give 3-ethoxy-6-hydroxy-2-methylbenzoic acid (114d, 0.168 g, 79% yield) as a salmon colored solid.

후처리

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customThe suspension was sonicated until homogeneous
  3. temperatureThe reaction mixture was heated at 95° C. for 1 hour
  4. temperatureThe reaction mixture was cooled to room temperature
  5. washwashed with 1N HCl and brine
  6. dry with materialThe organic layer was dried over Na2SO4
  7. concentrationconcentrated under vacuum

출처 및 근거

ORD 기록
ord-02955aef4c42479d9c7cf881469b90a7
출처 데이터셋
uspto-grants-2015_05
특허 번호
US09040515B2

반응 노트

불러오는 중…