Dimethyl Sulfate → HCID 21466119, compound

HRID 1940209Notes

Reaction equation

HRID 1940209 reaction equation
[CH3:1][C:2]1[C:3]([OH:11])=[C:4]([CH3:10])[C:5]([CH3:9])=[C:6]([CH:8]=1)[OH:7].[CH3:12][O:13]S(OC)(=O)=O.[C:19](=O)([O-])[O-].[K+].[K+].[OH-:25].[Na+]>CC(C)=O>[CH3:19][O:25][C:6]1([CH:8]=[C:2]([CH3:1])[C:3]([O:13][CH3:12])([OH:11])[C:4]([CH3:10])=[C:5]1[CH3:9])[OH:7]

Participants

6

Reactant 4

HCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 12785TrimethylhydroquinoneHCID 14798Sodium Hydroxide

Product 1

HCID 21466119HCID 21466119, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

A mixture of trimethylhydroquinone (60.87 g, 0.4 mol), dimethylsulfate (151.36 g, 1.2 mol) and potassium carbonate (221 g, 1.6 mol) in acetone (1.6 L) is refluxed for three days under nitrogen. After cooling, 10% sodium hydroxide (400 mL) is added and most of the acetone is evaporated. The black mixture is taken up in heptane (800 mL), the organic phase is separated and washed with 10% sodium hydroxide (2×200 mL), water (200 mL) and brine (200 mL). The solvent is dried (magnesium sulfate) and evaporated under reduced pressure to give a yellow oil. Purification on a small pad of silica gel eluting with heptane/ethyl acetate 95:5 gave 57.4 g (80%) of 1,4-dimethoxy-2,3,5-trimethylhydroquinone as a colorless oil which slowly crystallized.

Workup

  1. temperatureis refluxed for three days under nitrogen
  2. temperatureAfter cooling
  3. customis evaporated
  4. customthe organic phase is separated
  5. washwashed with 10% sodium hydroxide (2×200 mL), water (200 mL) and brine (200 mL)
  6. dry with materialThe solvent is dried (magnesium sulfate)
  7. customevaporated under reduced pressure
  8. customto give a yellow oil
  9. customPurification on a small pad of silica gel eluting with heptane/ethyl acetate 95:5

Sources & evidence

ORD record
ord-29d5f24ecf584ced892b9eea7ff6543c
Source dataset
uspto-grants-1997_12
Patent number
US05698696

Reaction notes

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