2-Methyl-4-nitrophenol → 2-Methyl-1-(2-methyl-4-nitrophenoxy)propan-2-ol

HRID 562596

反応式

HRID 562596 の反応式
[CH3:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[OH:11].[CH3:12][C:13]1([CH3:16])[CH2:15][O:14]1.C([O-])([O-])=O.[K+].[K+]>CC#N.O.C([O-])(O)=O.[Na+]>[CH3:12][C:13]([OH:14])([CH3:16])[CH2:15][O:11][C:3]1[CH:4]=[CH:5][C:6]([N+:8]([O-:10])=[O:9])=[CH:7][C:2]=1[CH3:1]

参加物

7

反応物 3

HCID 74422-Methyl-4-nitrophenolHCID 11208Isobutylene oxideHCID 11430Potassium Carbonate

生成物 1

HCID 575406062-Methyl-1-(2-methyl-4-nitrophenoxy)propan-2-ol収率 90.3%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6342Acetonitrile溶媒HCID 516892Sodium Bicarbonate溶媒

実験手順

A mixture of 2-methyl-4-nitrophenol (5.50 g, 35.9 mmol), 2,2-dimethyloxirane (7.77 g, 108 mmol), K2CO3 (4.96 g, 35.9 mmol) and NaH2PO4 (4.31 g, 35.9 mmol) in MeCN (50 mL) and H2O (8.82 mL) was stirred at 140° C. in a steel bomb for 6 hours. After cooling to RT, the reaction was diluted with aq. saturated NaHCO3 (80 ml) prior to extraction with EtOAc (100 ml). The EtOAc layer was dried over Na2SO4 and concentrated. The crude product was purified by silica gel chromatography employing a solvent gradient (hexane to 60% ethyl acetate) to elute 2-methyl-1-(2-methyl-4-nitrophenoxy)propan-2-ol (7.3 g, 32.4 mmol, 90% yield) as yellow oil. MS (M+1=226). 1H NMR (500 MHz, chloroform-d) δ ppm 8.00-8.15 (2H, m), 6.86 (1H, d, J=8.80 Hz), 3.90 (2H, s), 2.33 (3H, s), 1.40 (6H, s).

後処理

  1. extractionto extraction with EtOAc (100 ml)
  2. dry with materialThe EtOAc layer was dried over Na2SO4
  3. concentrationconcentrated
  4. customThe crude product was purified by silica gel chromatography

出典と根拠

ORDレコード
ord-4c1de9f843dd41b79fa4927fad584c96
出典データセット
uspto-grants-2011_11
特許番号
US08067420B2

関連ノート

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