Water → Vanillin

HRID 1021072ノート

反応式

HRID 1021072 の反応式
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

参加物

8

反応物 5

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

生成物 1

HCID 1183Vanillin収率 50%

試薬・触媒・溶媒 2

HCID 167845palladium(II) acetate触媒HCID 6228Dimethylformamide溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-ef5d74a95b68485fa9865873a85260c1
出典データセット
uspto-grants-2014_05
特許番号
US08716532B2

反応ノート

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