2-Methyl-2-butene → 2-Chloro-4-methoxy-5-(3-methoxy-propoxy)-benzoic acid

HRID 1158461

반응식

HRID 1158461 반응식
[Cl:1][C:2]1[CH:9]=[C:8]([O:10][CH3:11])[C:7]([O:12][CH2:13][CH2:14][CH2:15][O:16][CH3:17])=[CH:6][C:3]=1[CH:4]=[O:5].C([OH:22])(C)(C)C.C(Cl)Cl.CC(=CC)C.[O-]Cl=O.[Na+]>O.CC#N.CC#N.O>[Cl:1][C:2]1[CH:9]=[C:8]([O:10][CH3:11])[C:7]([O:12][CH2:13][CH2:14][CH2:15][O:16][CH3:17])=[CH:6][C:3]=1[C:4]([OH:22])=[O:5]

참가 물질

8

반응물 4

HCID 105532-Methyl-2-buteneHCID 18914702t-Butanol dichloromethaneHCID 23668197Sodium ChloriteHCID 592240102-Chloro-4-methoxy-5-(3-methoxy-propoxy)-benzaldehyde

생성물 1

HCID 595122372-Chloro-4-methoxy-5-(3-methoxy-propoxy)-benzoic acid

시약·촉매·용매 3

HCID 962Water용매2회HCID 6342Acetonitrile용매2회HCID 18373917Acetonitrile--water (1/1)용매

실험 절차

To a solution of 2-chloro-4-methoxy-5-(3-methoxy-propoxy)-benzaldehyde (1.08 g, 3.55 mmol) in a 3:1 mixture of tert-butanol/CH2Cl2 (20 mL) is added 2-methyl-2-butene (0.74 g, 5.32 mmol), followed by dropwise addition of a solution of NaClO2 (0.67g, 7.10 mmol) and NaH2PO4 (0.67 g, 4.26 mmol) in water (14 mL) over 15 min at room temperature, and stirring is continued overnight. The reaction mixture is poured into ice/saturated aqueous NaHCO3 solution, the water phase is washed with AcOEt. The ice-cold aqueous layer is acidified with HCl 37% to form a white precipitate which is filtered off, washed with ice-cold water and dried in vacuo. The compound is obtained as white solid. MS: 273.0 [M−H]+. tR (HPLC, Nucleosil C18HD column, 20-100% CH3CN/H2O/6 min, 100% CH3CN/2 min, CH3CN and H2O containing 0.1% TFA, flow: 1 mL/min): 3.25 min. 1H-NMR (CDCl3): δ 1.96 (m, 2H), 3.25 (s, 3H), 3.47 (m, 2H), 3.85 (s, 3H), 4.03 (m, 2H), 7.10 (s, 1H), 7.39 (s, 1H) ppm.

후처리

  1. additionThe reaction mixture is poured into ice/saturated aqueous NaHCO3 solution
  2. washthe water phase is washed with AcOEt
  3. customto form a white precipitate which
  4. filtrationis filtered off
  5. washwashed with ice-cold water
  6. customdried in vacuo
  7. customThe compound is obtained as white solid
  8. custom3.25 min

출처 및 근거

ORD 기록
ord-c8ed2c8768744fa8aef40a50a880b3f2
출처 데이터셋
uspto-grants-2010_10
특허 번호
US07807709B2

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