Hydrogen Peroxide → 2-Chloro-6-ethylbenzoic acid

HRID 844856노트

반응식

HRID 844856 반응식
[Cl:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([CH2:10][CH3:11])[C:3]=1[CH:4]=[O:5].P([O-])([O-])([O-])=[O:13].[Na+].[Na+].[Na+].OO.Cl([O-])=O.[Na+].S(=O)(O)[O-].[Na+]>C(#N)C.O>[Cl:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([CH2:10][CH3:11])[C:3]=1[C:4]([OH:13])=[O:5]

참가 물질

8

반응물 5

HCID 784Hydrogen PeroxideHCID 24243Trisodium PhosphateHCID 226137462-Chloro-6-ethylbenzaldehydeHCID 23665763Sodium BisulfiteHCID 23668197Sodium Chlorite

생성물 1

HCID 226137692-Chloro-6-ethylbenzoic acid수율 384.7%

시약·촉매·용매 2

HCID 962Water용매3회HCID 6342Acetonitrile용매

실험 절차

To a room temperature suspension of 2-chloro-6-ethylbenzaldehyde (13.5 mmol, 2.27 g) in acetonitrile (25 mL) was added a solution of monobasic sodium phosphate (3.4 mmol, 0.465 g) in water (7.5 mL) followed by hydrogen peroxide (1.8 mL, 30%). Then, a solution of sodium chlorite (23.7 mmol, 2.15 g) in water (20 mL) was added dropwise at 0° C. while maintaining the temperature below 3° C. After addition, the yellow suspension was stirred for 15 h at 0° C. to room temperature. At this time TLC analysis of the mixture indicated the absence of starting material. Then, a solution of sodium bisulfite (20.5 mmol, 2.8 g) in water (10 mL) was added dropwise at 0° C. until the yellow color disappeared (KI-paper positive). Cooling is essential to control the exothermic reaction. After 1 h, the solvent was removed under vacuum. The neutral impurities were extracted with diethyl ether (200 mL). Then, the basic aqueous solution was neutralized with 10% HCl to pH ˜1. The precipitated white solid was collected by filtration and dried at in air to afford 2.415 g (97% yield) of 2-chloro-6-ethylbenzoic acid as an amorphous white solid. EI-HRMS m/e calcd for C9H9ClO2 (M+) 184.0291, found 184.0295.

후처리

  1. temperaturewhile maintaining the temperature below 3° C
  2. additionAfter addition
  3. temperatureCooling
  4. customthe exothermic reaction
  5. waitAfter 1 h
  6. customthe solvent was removed under vacuum
  7. extractionThe neutral impurities were extracted with diethyl ether (200 mL)
  8. filtrationThe precipitated white solid was collected by filtration
  9. customdried at in air

출처 및 근거

ORD 기록
ord-885d5a7070814e72bbd1fe6c6b607137
출처 데이터셋
uspto-grants-2002_04
특허 번호
US06380387B1

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