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

HRID 1158458

반응식

HRID 1158458 반응식
[CH3:1][O:2][C:3]1[C:10]([O:11][CH2:12][CH2:13][CH2:14][O:15][CH3:16])=[CH:9][C:6]([CH:7]=[O:8])=[C:5]([CH3:17])[CH:4]=1.C([OH:22])(C)(C)C.C(Cl)Cl.CC(=CC)C.[O-]Cl=O.[Na+]>O.CCOCC>[CH3:1][O:2][C:3]1[C:10]([O:11][CH2:12][CH2:13][CH2:14][O:15][CH3:16])=[CH:9][C:6]([C:7]([OH:22])=[O:8])=[C:5]([CH3:17])[CH:4]=1

참가 물질

7

반응물 4

HCID 105532-Methyl-2-buteneHCID 18914702t-Butanol dichloromethaneHCID 23668197Sodium ChloriteHCID 592239044-Methoxy-5-(3-methoxy-propoxy)-2-methyl-benzaldehyde

생성물 1

HCID 595123794-Methoxy-5-(3-methoxy-propoxy)-2-methyl-benzoic acid

시약·촉매·용매 2

HCID 962Water용매HCID 3283Diethyl Ether용매

실험 절차

To a solution of 4-methoxy-5-(3-methoxy-propoxy)-2-methyl-benzaldehyde (1.25 g, 5.25 mmol) in a 3:1 mixture of tert-butanol/CH2Cl2 (60 mL) is added 2-methyl-2-butene (25.0 mL), followed by dropwise addition of a solution of NaClO2 (5.81 g, 51.4 mmol) and NaH2PO4 (4.07 g, 33.6 mmol) in water (45 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, then acidified and extracted with AcOEt. The combined organics are washed with brine, dried (Na2SO4) and concentrated to give a yellow solid. The crude product is stirred for 30 min in a 95:5 mixture of hexaneldiisopropyl ether (25 mL), the precipitate is filtered off, washed with a 95:5 mixture of hexane/diisopropyl ether and dried to give the title compound as yellowish solid. MS: 253.0 [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): 3.23 min. 1H-NMR (CDCl3): δ 1.96 (m, 2H), 2.51 (s, 3H), 3.27 (s, 3H), 3.48 (m, 2H), 3.84 (s, 3H), 4.00 (m, 2H), 6.89 (s, 1H), 7.41 (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. extractionextracted with AcOEt
  4. washThe combined organics are washed with brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated
  7. customto give a yellow solid
  8. filtrationthe precipitate is filtered off
  9. washwashed with a 95:5 mixture of hexane/diisopropyl ether
  10. customdried

출처 및 근거

ORD 기록
ord-62cccaaf728244f1bdc659ab9e5fb907
출처 데이터셋
uspto-grants-2010_10
특허 번호
US07807709B2

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