Sodium Hydroxide → Dimethyl Sulfate

HRID 1421202Notes

Reaction equation

HRID 1421202 reaction equation
FC(F)(F)[S:3]([O-:6])(=[O:5])=[O:4].C1C2C(=CC3C(C=2[S+](CCCC)C)=CC=CC=3)C=CC=1.F[C:30](F)(F)S([O-])(=O)=O.[OH-].[Na+].[CH3:39][O:40][C:41]1[C:42]2[C:47]([CH:48]=[C:49]3[C:54]=1[CH:53]=[CH:52][CH:51]=[CH:50]3)=[CH:46][CH:45]=[CH:44][CH:43]=2>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.ClCCl.O>[CH:53]1[C:54]2[C:41](=[O:40])[C:42]3[C:47](=[CH:46][CH:45]=[CH:44][CH:43]=3)[CH2:48][C:49]=2[CH:50]=[CH:51][CH:52]=1.[CH3:30][O:6][S:3]([O:40][CH3:41])(=[O:5])=[O:4].[CH3:39][O:40][C:41]1[C:42]2[C:47]([CH:48]=[C:49]3[C:54]=1[CH:53]=[CH:52][CH:51]=[CH:50]3)=[CH:46][CH:45]=[CH:44][CH:43]=2

Participants

10

Reactant 4

HCID 14798Sodium HydroxideHCID 169659-MethoxyanthraceneHCID 2758875Trifluoromethanesulfonate2×HCID 18780403HCID 18780403, compound

Product 3

HCID 6497Dimethyl SulfateHCID 7018AnthroneHCID 169659-Methoxyanthracene

Reagents, catalysts & solvents 3

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 962WaterSolvent2×HCID 6344DichloromethaneSolvent

Procedure

Preparation of 9-anthryl n-butyl methyl sulfonium trifluoromethanesulfonate, wherein trifluoromethanesulfonate and triflate are synonymous and R1 was n-butyl, R2 was methyl, X- was CF3 (CF2)nSO3-, and n was 0. A solution of 25.0 g (129 millimoles (mM)) of anthrone, 32.5 g (24.4 milliliters (mL), 257 mM) of dimethylsulfate, and 0.5 g of benzyl triethylammonium chloride was prepared in 250 mL of dichloromethane and 100 mL of water. Next, 80 g (1 M) of 50% sodium hydroxide was dripped into this solution with rapid stirring. GC analysis of the reaction immediately after the addition determined essentially complete conversion to 9-methoxyanthracene. After stirring for 1 hour the water layer was discarded, the organic layer washed with 5% aqueous HCl, then saturated sodium bicarbonate, dried with magnesium sulfate, then evaporated to give a faintly yellow solid. The solid was then recrystallized from heptane to give 9-methoxyanthracene.

Workup

  1. customGC analysis of the reaction
  2. additionimmediately after the addition
  3. washthe organic layer washed with 5% aqueous HCl
  4. dry with materialsaturated sodium bicarbonate, dried with magnesium sulfate
  5. customevaporated
  6. customto give a faintly yellow solid
  7. customThe solid was then recrystallized from heptane

Sources & evidence

ORD record
ord-d6e0a2237af541b9acdabc9249f49ac2
Source dataset
uspto-grants-2000_06
Patent number
US06074800

Reaction notes

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