P-Cresol → 1-(2,2-Dimethylpropoxy)-4-methylbenzene

HRID 911447Notes

Reaction equation

HRID 911447 reaction equation
[CH:1]1[C:6]([OH:7])=[CH:5][CH:4]=[C:3]([CH3:8])[CH:2]=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH2:42](O)[C:43]([CH3:46])([CH3:45])[CH3:44]>C1COCC1>[CH3:42][C:43]([CH3:46])([CH3:45])[CH2:44][O:7][C:6]1[CH:5]=[CH:4][C:3]([CH3:8])=[CH:2][CH:1]=1

Participants

6

Reactant 4

HCID 2879P-CresolHCID 6404Neopentyl alcoholHCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylate

Product 1

HCID 178359711-(2,2-Dimethylpropoxy)-4-methylbenzene

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of p-cresol (526 mg, 4.87 mmol) in THF (50 mL), add with stirring diisopropyl azodicarboxylate (2.16 mL, 10.7 mmol) followed by triphenylphosphine (306 mg, 11.7 mmol) and neopentyl alcohol (5.15 g, 58.4 mmol). Heat at 60° C. for 3 h, cool to ambient temperature and concentrate in vacuo. Purify by chromatography on silica gel eluting with hexane/EtOAc to give the desired intermediate as a colorless oil.

Workup

  1. temperaturecool to ambient temperature
  2. concentrationconcentrate in vacuo
  3. customPurify by chromatography on silica gel eluting with hexane/EtOAc

Sources & evidence

ORD record
ord-8fc367222dc347828e622b9ce3e701ec
Source dataset
uspto-grants-2011_09
Patent number
US08022062B2

Reaction notes

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