Dimethyl Sulfate → HCID 54076170, compound

HRID 1940214Notes

Reaction equation

HRID 1940214 reaction equation
[OH:1][C:2]1[C:3]([CH3:16])=[C:4]([CH3:15])[C:5]2[O:9][C:8]([CH3:11])([CH3:10])[C:7](=[O:12])[C:6]=2[C:13]=1[CH3:14].[C:17]1(O)C=CC=CC=1.COS(OC)(=O)=O.C(=O)([O-])[O-].[K+].[K+].[OH-].[Na+]>CC(C)=O>[CH3:17][O:1][C:2]1[C:3]([CH3:16])=[C:4]([CH3:15])[C:5]2[O:9][C:8]([CH3:10])([CH3:11])[C:7](=[O:12])[C:6]=2[C:13]=1[CH3:14]

Participants

6

Reactant 4

HCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 21466120HCID 21466120, compound

Product 1

HCID 54076170HCID 54076170, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

A mixture of phenol 5-hydroxy-2,2,4,6,7-pentamethyl-2,3-dihydro-1-benzofuran-3-one (7.16 g, 32.54 mmol), dimethylsulfate (6.16 g, 48.8 mmol) and potassium carbonate (13.5 g, 97.63 mmol) in acetone (160 mL) is refluxed under nitrogen for 3 days. After cooling, 3N sodium hydroxide (100 mL) is added and most of the acetone is evaporated under reduced pressure. The mixture is extracted with ethyl acetate (200 mL) and the organic layer is washed with 3N sodium hydroxide (2×100 mL), water, brine, dried (magnesium sulfate)and evaporated to dryness to give 7.52 g (99%) of 5-methoxy-2,2,4,6,7-pentamethyl-2,3-dihydro-1-benzofuran-3-one as a yellow solid which is used without purification for the next step. Rf=0.4 (heptane/ethyl acetate 90:10)

Workup

  1. temperatureis refluxed under nitrogen for 3 days
  2. temperatureAfter cooling
  3. customis evaporated under reduced pressure
  4. extractionThe mixture is extracted with ethyl acetate (200 mL)
  5. washthe organic layer is washed with 3N sodium hydroxide (2×100 mL), water, brine, dried (magnesium sulfate)and
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-e82e3bc0330f467cac23ce0865b1db41
Source dataset
uspto-grants-1997_12
Patent number
US05698696

Reaction notes

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