Hydrochloric Acid → 4-(1,2,2,6,6-Pentamethyl-1,2,3,6-tetrahydropyridin-4-yl)-phenol

HRID 237745

反応式

HRID 237745 の反応式
[CH3:1][N:2]1[C:7]([CH3:9])([CH3:8])[CH2:6][C:5](=O)[CH2:4][C:3]1([CH3:12])[CH3:11].[C:13]1([OH:19])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.Cl.[OH-].[NH4+]>>[CH3:1][N:2]1[C:7]([CH3:9])([CH3:8])[CH:6]=[C:5]([C:16]2[CH:17]=[CH:18][C:13]([OH:19])=[CH:14][CH:15]=2)[CH2:4][C:3]1([CH3:12])[CH3:11]

参加物

5

反応物 4

HCID 313Hydrochloric AcidHCID 996PhenolHCID 14923Ammonium HydroxideHCID 2419551,2,2,6,6-Pentamethyl-4-piperidone

生成物 1

HCID 685241834-(1,2,2,6,6-Pentamethyl-1,2,3,6-tetrahydropyridin-4-yl)-phenol収率 34%

反応条件

温度
70 °C

実験手順

1,2,2,6,6-Pentamethyl-piperidin-4-one (8.64 g, 50.00 mmol) and phenol (4.98 g, 53.00 mmol) were melted together at 60° C. in a 100 mL round bottomed flask after which 13.5 mL of concentrated hydrochloric acid was added dropwise. The yellow solution was stirred at 70° C. for 24 hours. The mixture was poured into a beaker containing ice. Ammonium hydroxide was added carefully while stirring until the pH reached 7˜8. The mixture was extracted with EtOAc five times. The organic phases were combined, dried (Na2SO4) and concentrated. The residue was purified by chromatography on a silica gel column, eluting with 7N NH3 in methanol/dichloromethane to give 4-(1,2,2,6,6-pentamethyl-1,2,3,6-tetrahydropyridin-4-yl)-phenol (4.11 g, 34%).

後処理

  1. additionThe mixture was poured into a beaker
  2. additioncontaining ice
  3. stirringwhile stirring until the pH
  4. extractionThe mixture was extracted with EtOAc five times
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated
  7. customThe residue was purified by chromatography on a silica gel column
  8. washeluting with 7N NH3 in methanol/dichloromethane

出典と根拠

ORDレコード
ord-f69f7ec3095f4145ab52f743f9a5268d
出典データセット
uspto-grants-2014_02
特許番号
US08642603B2

関連ノート

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