Trifluoroacetic acid → 1-(2,2-Dimethylpropyl)-4-[(prop-2-en-1-yl)oxy]benzene

HRID 2113145Notes

Reaction equation

HRID 2113145 reaction equation
[CH2:1]([O:4][C:5]1[CH:10]=[CH:9][C:8]([CH:11](O)[C:12]([CH3:15])([CH3:14])[CH3:13])=[CH:7][CH:6]=1)[CH:2]=[CH2:3].C[SiH](C)C.FC(F)(F)C(O)=O>ClCCl>[CH2:1]([O:4][C:5]1[CH:6]=[CH:7][C:8]([CH2:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[CH:9][CH:10]=1)[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 70435TrimethylsilaneHCID 69050404HCID 69050404, compound

Product 1

HCID 690512221-(2,2-Dimethylpropyl)-4-[(prop-2-en-1-yl)oxy]benzene

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-(4-Allyloxyphenyl)-2,2-dimethylpropan-1-ol (1.2 g, 6.1 mmol) and trimethylsilane (mL, 61.0 mmol) were dissolved in dichloromethane (5.0 mL) and trifluoroacetic acid (2.1 g, 18.3 mmol) was added at 0° C. After 30 min, the reaction mixture was concentrated to give esentially pure 1-allyloxy-4-neopentylbenzene. The crude product was dissolved in 1,2,4-trichlorobenzene (5.0 mL) and the solution was heated to reflux for 4 hrs. Removal of solvent and chromatography of the residue on silica gel eluting with 9:1 hexane:ethyl acetate gave 0.70 g 2-allyl-4-(2,2-dimethyl-propyl)phenol.

Workup

  1. concentrationthe reaction mixture was concentrated

Sources & evidence

ORD record
ord-ec3c0f558bb74ef9863a92d27136c89f
Source dataset
uspto-grants-2009_04
Patent number
US07524882B2

Reaction notes

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