Methyl iodide → 1,4-Dimethoxy-2,3,5-trimethyl-benzene

HRID 63805

Reaction equation

HRID 63805 reaction equation
[CH3:1][C:2]1[C:7]([CH3:8])=[C:6](O)[C:5]([CH3:10])=[CH:4][C:3]=1[OH:11].[C:12](=[O:15])([O-])[O-].[K+].[K+].[CH3:18]I>CCC(C)=O>[CH3:18][O:11][C:3]1[CH:4]=[C:5]([CH3:10])[C:6]([O:15][CH3:12])=[C:7]([CH3:8])[C:2]=1[CH3:1]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 12785Trimethylhydroquinone

Product 1

HCID 109240691,4-Dimethoxy-2,3,5-trimethyl-benzeneYield 80%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Conditions

Temperature
65 °C

Procedure

A 2 L 3-N flask was charged with 2,3,5-trimethyl-benzene-1,4-diol (Ex-1B-1) (50 g, 0.33 mol) and MEK (750 mL) to yield an amber solution. Potassium carbonate (210 g, 1.64 mol) was charged to the solution. After 30 min at RT, MeI (81.2 mL, 1.31 mol) was added to the brown suspension. The reaction mixture was heated to 65° C. for 72 h. After cooling to RT, the reaction mixture was concentrated to dryness by rotary evaporation to give a white paste. The paste was washed with EtOAc (3×300 mL). The EtOAc extracts were combined and concentrated by rotary evaporation. The resulting yellow-brown oil was chromatographed (80:20/Heptanes:EtOAc) to yield 1,4-dimethoxy-2,3,5-trimethyl-benzene (Ex-1B-2) (47.2 g, 80%). 1H NMR (400 MHz, CDCl3) δ (ppm): 6.55 (s, 1H), 3.80 (s, 3H), 3.68 (s, 3H), 2.30 (s, 3H), 2.22 (s, 3H), 2.14 (s, 3H).

Workup

  1. customto yield an amber solution
  2. temperatureAfter cooling to RT
  3. concentrationthe reaction mixture was concentrated to dryness by rotary evaporation
  4. customto give a white paste
  5. washThe paste was washed with EtOAc (3×300 mL)
  6. concentrationconcentrated by rotary evaporation
  7. customThe resulting yellow-brown oil was chromatographed (80:20/Heptanes:EtOAc)

Sources & evidence

ORD record
ord-f22cc835cbb4410194837ee083966fe1
Source dataset
uspto-grants-2016_09
Patent number
US09447006B2

Linked notes

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