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

HRID 2041328Notes

Reaction equation

HRID 2041328 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-a1282136201a4c22a76c3ded4f5ff2d9
Source dataset
uspto-grants-2013_11
Patent number
US08580780B2

Reaction notes

Loading…