Dimethyl Sulfate → HCID 10773603, compound

HRID 1889290Notes

Reaction equation

HRID 1889290 reaction equation
[F:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([OH:12])=[CH:4][CH:3]=1.[C:13](=O)([O-])[O-].[K+].[K+].S(OC)(OC)(=O)=O>CC(C)=O>[F:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([O:12][CH3:13])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 109208304-fluoronaphthalen-1-ol

Product 1

HCID 10773603HCID 10773603, compoundYield 48.4%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

21.7 g of 4-Fluoro-naphthalen-1-ol were dissolved in 250 ml acetone. 39.0 g of potassium carbonate and 14.6 ml dimethyl sulfate were added at room temperature. The reaction was placed under nitrogen and stirred for 72 h. The mixture was filtrated, the solid washed with acetone, and the filtrate was concentrated to a viscous oil, which was taken up in ethyl acetate. This was washed with water and with brine, dried over sodium sulfate, filtered through celite and concentrated. The resulting oil was distilled using a Kugelrohr-apparatus, yielding 11.4 g of 4-fluoro-1-methoxynaphthalene.

Workup

  1. filtrationThe mixture was filtrated
  2. washthe solid washed with acetone
  3. concentrationthe filtrate was concentrated to a viscous oil, which
  4. washThis was washed with water and with brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered through celite and
  7. concentrationconcentrated
  8. distillationThe resulting oil was distilled

Sources & evidence

ORD record
ord-37479825d2c5453387272503f4be0e13
Source dataset
uspto-grants-2013_08
Patent number
US08501981B2

Reaction notes

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