Toluene → 2-Acetoxy-6-methoxytoluene

HRID 1640068Notes

Reaction equation

HRID 1640068 reaction equation
[C:1]([O:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([OH:11])[C:6]=1[CH3:12])(=[O:3])[CH3:2].[C:13](=O)([O-])[O-].[K+].[K+].CI.C1(C)C=CC=CC=1>C(#N)C.O>[C:1]([O:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([O:11][CH3:13])[C:6]=1[CH3:12])(=[O:3])[CH3:2]

Participants

7

Reactant 4

HCID 1140TolueneHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 234694162-Methylresorcinol, acetate

Product 1

HCID 594394662-Acetoxy-6-methoxytolueneYield 86.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
90 °C

Procedure

A solution of 5.01 g (30.0 mmol) of 2-acetoxy-6-hydroxytoluene in 50 mL of acetonitrile was added with 12.44 g (90.0 mmol) of potassium carbonate and 12.77 g (90.0 mmol) of methyl iodide and heated and stirred on a 90° C. oil bath for 96 minutes. The reaction mixture which had been allowed to stand at room temperature for about 3 hours was added to a mixture of 100 mL of toluene and 100 mL of water stirred on an ice-water bath, and after stirred for two minutes, transferred to a separatory funnel and then settled. The aqueous layer was separated and discarded and after the organic layer was washed with 20 mL of 1 N aqueous sodium hydroxide and 20 mL of water three times, and the solvent was evaporated to obtain 4.69 g of title compound.

Workup

  1. temperatureheated
  2. waitto stand at room temperature for about 3 hours
  3. stirringstirred on an ice-water bath
  4. stirringafter stirred for two minutes
  5. customtransferred to a separatory funnel
  6. customThe aqueous layer was separated
  7. washafter the organic layer was washed with 20 mL of 1 N aqueous sodium hydroxide and 20 mL of water three times
  8. customthe solvent was evaporated

Sources & evidence

ORD record
ord-7a671e334177414e9fe32a87fcf6ba44
Source dataset
uspto-grants-2012_02
Patent number
US08110688B2

Reaction notes

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