Phenol → 2-Isobutylphenol

HRID 381812

Reaction equation

HRID 381812 reaction equation
[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]

Participants

8

Reactant 5

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

Product 2

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

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-9427f415bad94af8b5b9dc4a09e50c74
Source dataset
uspto-grants-2001_10
Patent number
US06307107B1

Linked notes

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