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

HRID 562596

반응식

HRID 562596 반응식
[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]

참가 물질

7

반응물 3

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

생성물 1

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

시약·촉매·용매 3

HCID 962Water용매HCID 6342Acetonitrile용매HCID 516892Sodium Bicarbonate용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-4c1de9f843dd41b79fa4927fad584c96
출처 데이터셋
uspto-grants-2011_11
특허 번호
US08067420B2

연결된 노트

불러오는 중…