Phenol → 2-Isobutylphenol

HRID 381812

反応式

HRID 381812 の反応式
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH:8][C:9]([CH3:19])([CH3:18])[C:10]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:11].FC(F)(F)C(O)=O.C([SiH](CC)CC)C.C(=O)(O)[O-].[Na+]>CCOCC>[OH:8][C:9]([CH3:19])([CH3:18])[C:10]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:11].[CH2:10]([C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][C:1]=1[OH:7])[CH:9]([CH3:19])[CH3:18]

参加物

8

反応物 5

HCID 996PhenolHCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 819842-Hydroxy-2-methyl-1-phenylpropan-1-oneHCID 516892Sodium Bicarbonate

生成物 2

HCID 819842-Hydroxy-2-methyl-1-phenylpropan-1-oneHCID 931442-Isobutylphenol収率 55%

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒

実験手順

2-Hydroxy-isobutyrophenone was prepared from phenol following the procedure described in Canadian Journal of Chemistry, 31, 1956, 851. To a solution of 2-hydroxy-isobutyrophenone (2g, 12.2 mmol) in trifluroacetic acid (14 g, 122 mmol) was slowly added triethylsilane (26.8 mmol). The solution was stirred at room temperature for 6 hours. Saturated sodium bicarbonate solution was added to the reaction mixture, followed by ether. The layers were separated, and the aqueous layer was extracted with ether. The organic layers were combined, dried over magnesium sulfate, and concentrated. The crude material was distilled under vacuum (about 9.3×10−4 MPa, 75° C.). The distillate was washed with potassium hydroxide solution, followed by addition of hydrogen chloride solution, and extraction with ether. The ether layers were combined, dried over magnesium sulfate, and concentrated to give 1.0 g (55%) of 2-isobutylphenol. 1H NMR (300 Mhz, δ, CDCl3): 7.0 (m, 2H), 6.8 (t, 1H), 6.7 (d, 1H), 4.6 (br. s, 1H), 2.4 (d, 2H), 1.9 (s, 1H), 0.9 (d, 6H).

後処理

  1. customThe layers were separated
  2. extractionthe aqueous layer was extracted with ether
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated
  5. distillationThe crude material was distilled under vacuum (about 9.3×10−4 MPa, 75° C.)
  6. washThe distillate was washed with potassium hydroxide solution
  7. additionfollowed by addition of hydrogen chloride solution, and extraction with ether
  8. dry with materialdried over magnesium sulfate
  9. concentrationconcentrated

出典と根拠

ORDレコード
ord-9427f415bad94af8b5b9dc4a09e50c74
出典データセット
uspto-grants-2001_10
特許番号
US06307107B1

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