2-(2-Methoxy-6-methylphenyl)-2-propanol → 2-Iso-propyl-3-methylanisole

HRID 1170955Notes

Reaction equation

HRID 1170955 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([CH3:9])[C:4]=1[C:10](O)([CH3:12])[CH3:11]>C(OCC)(=O)C.C(O)(=O)C>[CH:10]([C:4]1[C:5]([CH3:9])=[CH:6][CH:7]=[CH:8][C:3]=1[O:2][CH3:1])([CH3:12])[CH3:11]

Participants

3

Reactant 1

HCID 666426962-(2-Methoxy-6-methylphenyl)-2-propanol

Product 1

HCID 210341322-Iso-propyl-3-methylanisoleYield 100%

Reagents, catalysts & solvents 1

HCID 22609514Ethyl acetate acetateSolvent

Procedure

A solution of 2-(2-methoxy-6-methylphenyl)-2-propanol (0.50 g, 2.77 mmol) in ethyl acetate-acetic acid (9:1, 10.0 mL) at room temperature was stirred under a H2 atmosphere for 16 h. The mixture was filtered through a Celite plug and the solvent was removed under reduced pressure. The residue was dissolved in hexanes and washed with water. The organic layer was dried MgSO4, filtered and concentrated under reduced pressure to afford 2-iso-propyl-3-methylanisole (0.45 g, 100%) as colorless oil, which was used for the next step without further purification: 1H NMR (300 MHz, DMSO-d6): δ 7.01 (dd, J=12.0 Hz, 11.7 Hz, 1 H), 6.78 (d, J=12.0 Hz, 1 H), 6.70 (d, J=11.7 Hz, 1 H), 3.74 (s, 3 H), 3.28 (m, 1 H), 2.26 (s, 3 H), 1.24 (d, J=10.8 Hz, 6 H); TLC conditions: Uniplate silica gel, 250 microns; Mobile phase=ethyl acetate-hexanes (1:9); Rf=0.80.

Workup

  1. filtrationThe mixture was filtered through a Celite plug
  2. customthe solvent was removed under reduced pressure
  3. dissolutionThe residue was dissolved in hexanes
  4. washwashed with water
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-8fd4988998b64b9d8dca6d43b9a17051
Source dataset
uspto-grants-2010_11
Patent number
US07829552B2

Reaction notes

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