Dimethyl Sulfate → Benzene, 1-(1,1-dimethylethyl)-2-methoxy-3-methyl-

HRID 259577

Reaction equation

HRID 259577 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([CH3:11])[C:6]=1[OH:12])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+].[CH3:15]OS(OC)(=O)=O.C(=O)([O-])[O-].[Na+].[Na+]>O>[C:1]([C:5]1[C:6]([O:12][CH3:15])=[C:7]([CH3:11])[CH:8]=[CH:9][CH:10]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 6497Dimethyl SulfateHCID 10340Sodium CarbonateHCID 14798Sodium HydroxideHCID 166782-tert-Butyl-6-methylphenol

Product 1

HCID 521940Benzene, 1-(1,1-dimethylethyl)-2-methoxy-3-methyl-

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
95 °C

Procedure

A mixture of 0.12 mole of 2-t-butyl-6-methylphenol and 12.0 ml. of 10.0 N sodium hydroxide solution is stirred and heated on the steam bath for 1 hour. The water is evaporated in vacuo. The residue is added portion-wise with stirring to 0.24 mole of dimethylsulfate and the mixture is stirred at 95° C. for 6 hours and at room temperature for 15 hours. Sodium carbonate (0.25 mole) in 100 ml. of water is added and stirring is continued for 5 hours. The mixture is extracted with 3 × 100 ml. of ether and the extract is dried and concentrated to dryness to give 3-t-butyl-2-methoxytoluene.

Workup

  1. temperatureheated on the steam bath for 1 hour
  2. customThe water is evaporated in vacuo
  3. additionThe residue is added portion-wise
  4. stirringstirring
  5. waitis continued for 5 hours
  6. extractionThe mixture is extracted with 3 × 100 ml
  7. dry with materialof ether and the extract is dried
  8. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-4fed5174c3714499bd54c213547cb077
Source dataset
uspto-grants-1977_07
Patent number
US04038396

Linked notes

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