Methanol → 4-Ethylresorcinol

HRID 1072948ノート

反応式

HRID 1072948 の反応式
[CH3:1][C:2]([C:4]1[CH:5]=[CH:6][C:7]([OH:11])=[CH:8][C:9]=1[OH:10])=O.CO.[H][H]>[Ni].[Pd].C(O)(=O)C>[CH2:2]([C:4]1[CH:5]=[CH:6][C:7]([OH:11])=[CH:8][C:9]=1[OH:10])[CH3:1]

参加物

7

反応物 3

HCID 887MethanolHCID 69902',4'-DihydroxyacetophenoneHCID 178418361HCID 178418361、化合物

生成物 1

HCID 179274-Ethylresorcinol

試薬・触媒・溶媒 3

HCID 935Nickel触媒HCID 23938Palladium触媒HCID 176Acetic Acid溶媒

反応条件

温度
72.5 °C

実験手順

2,4-Dihydroxy acetophenone (76 g, 0.5 mole) was charged in a 1 liter autoclave reactor along with methanol (300 ml), acetic acid (5 ml), and Raney Nickel (15.2 g washed several times with water and water/methanol) and 750 mg of Pd/C. The pH of the system was 5.0. The autoclave was checked for leaks with nitrogen. The autoclave was pressurized to 500 psi with hydrogen and stirred at 70-75° C. up to 8 hrs. During this time 97% of the theoretical value for hydrogen was consumed. The reaction was vented and the contents were filtered through a milipore filter to give a yellow solution. Concentration of this solution in vacuo gave a solid. This solid was crystalized from 1,2-dichloroethane to give 4-ethyl resorcinol in 85% isolated yield. The unreacted 2,4-dihydroxy acetophenone was recovered (−13%) from the reaction mixture and was recycled. The structure of 4-ethyl resorcinol and 2,4-dihydroxy acetophenone were characterized by NMR (see FIG. 1), Gas Chromatography (see FIG. 2), IR (See FIG. 3) and Mass spectroscopy. The mass spectroscopy indicated that the mass was 138.

後処理

  1. customDuring this time 97% of the theoretical value for hydrogen was consumed
  2. filtrationthe contents were filtered through a milipore
  3. filtrationfilter
  4. customto give a yellow solution
  5. customConcentration of this solution in vacuo gave a solid
  6. customThis solid was crystalized from 1,2-dichloroethane

出典と根拠

ORDレコード
ord-0785870683a348adabc3f32bf6bacb96
出典データセット
uspto-grants-2005_06
特許番号
US06911562B2

反応ノート

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