Water → Vanillin

HRID 1021072

반응식

HRID 1021072 반응식
C[O:2][C:3]1C=C(C=CC=1)C=C.I[C:12]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=1.N1CCCCC1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[OH2:45]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.CN(C=O)C>[O:2]=[CH:3][C:17]1[CH:12]=[CH:13][C:14]([OH:45])=[C:15]([O:18][CH3:19])[CH:16]=1

참가 물질

8

반응물 5

HCID 962WaterHCID 8082PiperidineHCID 11776TriphenylphosphineHCID 696764-IodoanisoleHCID 5841461-Ethenyl-3-methoxybenzene

생성물 1

HCID 1183Vanillin수율 50%

시약·촉매·용매 2

HCID 167845palladium(II) acetate촉매HCID 6228Dimethylformamide용매

실험 절차

The obtained 4-hydroxy, 3-methoxystyrene was taken in a 100 ml round bottom flask fitted with a condenser and mixed with para-iodo anisole (1.9 mmol), piperidine (4.5 mmol), palladium acetate (0.076 mmol), triphenylphosphine (0.089 mmol) and DMF (20 ml). The flask was shaken well and placed inside the monomode microwave oven and irradiated (250 W, 160° C.) for 30 minutes in parts. After completion, the reaction mixture was poured in ice cooled water and extracted with ethyl acetate. The organic layer was washed with dil. HCl, brine and water and dried over sodium sulphate. The solvent was evaporated under reduced pressure to obtain liquid which was purified on silica gel by column chromatography using a mixture of hexane and ethyl acetate (9:1 to 6:4) provided a white solid; 50% yield (20% overall yield starting from vanillin) (m.p. 163-166° C.); 1H NMR (CDCl3) δ 7.37 (2H, d), 6.95 (2H, d,), 6.84 (5H, m), 3.88 (3H, s), 3.76 (3H, s); 13C NMR (CDCl3) δ 159.0, 146.7, 145.3, 130.4, 127.4, 126.6, 126.1, 120.1, 114.5, 114.1, 108.0, 55.9 and 55.3.

후처리

  1. customfitted with a condenser
  2. customirradiated (250 W, 160° C.) for 30 minutes in parts
  3. additionAfter completion, the reaction mixture was poured in ice
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with dil. HCl, brine and water
  6. dry with materialdried over sodium sulphate
  7. customThe solvent was evaporated under reduced pressure
  8. customto obtain liquid which
  9. customwas purified on silica gel by column chromatography
  10. additiona mixture of hexane and ethyl acetate (9:1 to 6:4)
  11. customprovided a white solid

출처 및 근거

ORD 기록
ord-ef5d74a95b68485fa9865873a85260c1
출처 데이터셋
uspto-grants-2014_05
특허 번호
US08716532B2

연결된 노트

불러오는 중…