Dimethyl Sulfate → tert-Butylanisole

HRID 1174078Notes

Reaction equation

HRID 1174078 reaction equation
COS([O:6][CH3:7])(=O)=O.[C:8]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1O)([CH3:11])([CH3:10])[CH3:9].[OH-].[Na+]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C(Cl)Cl>[C:8]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[O:6][CH3:7])([CH3:11])([CH3:10])[CH3:9]

Participants

6

Reactant 3

HCID 6497Dimethyl SulfateHCID 69232-Tert-ButylphenolHCID 14798Sodium Hydroxide

Product 1

HCID 270626tert-Butylanisole

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 6344DichloromethaneSolvent

Procedure

Dimethylsulfate (56.7 g, 0.45 mol) was added at room temperature to a well-stirred mixture of 2-tert-butylphenol (45 g, 0.3 mol), CH2Cl2 (200 ml), 40% aq. NaOH (200 ml) and tetrabutylammonium bromide (1 g). After 16 h of stirring, the organic phase was separated, washed with H2O, dried over MgSO4, evaporated and distilled at 110-112° C./10 Torr. Yield 35 g (71%).

Workup

  1. customthe organic phase was separated
  2. washwashed with H2O
  3. dry with materialdried over MgSO4
  4. customevaporated
  5. distillationdistilled at 110-112° C./10 Torr

Sources & evidence

ORD record
ord-7b013c4d5af44a8aa3faa5907fc81757
Source dataset
uspto-grants-2010_11
Patent number
US07834205B2

Reaction notes

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