Chlorotrimethylsilane → Methyl 5-methylsalicylate

HRID 1531928Notes

Reaction equation

HRID 1531928 reaction equation
[CH3:1][C:2]1[CH:10]=[C:6]([C:7]([OH:9])=[O:8])[C:5]([OH:11])=[CH:4][CH:3]=1.[CH3:12][Si](Cl)(C)C>CO>[OH:11][C:5]1[CH:4]=[CH:3][C:2]([CH3:1])=[CH:10][C:6]=1[C:7]([O:9][CH3:12])=[O:8]

Participants

4

Reactant 2

HCID 6397Chlorotrimethylsilane2×HCID 69735-Methylsalicylic acid

Product 1

HCID 89802Methyl 5-methylsalicylate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 5-methylsalicylic acid (7.24 g) in methanol (250 ml) was added trimethylsilyl chloride (60 ml). The mixture was heated at reflux for 2 hours and stirred at room temperature overnight. A further 60 ml trimethylsilyl chloride was added and the mixture heated at reflux for 6 hours. The mixture was evaporated and the residue partitioned between ethyl acetate and saturated aqueous sodium bicarbonate. The organic phase was dried (MgSO4) and evaporated to give the crude product. Yield 5.87 g. Used directly in the next step.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 2 hours
  3. temperaturethe mixture heated
  4. temperatureat reflux for 6 hours
  5. customThe mixture was evaporated
  6. customthe residue partitioned between ethyl acetate and saturated aqueous sodium bicarbonate
  7. dry with materialThe organic phase was dried (MgSO4)
  8. customevaporated

Sources & evidence

ORD record
ord-ccd19e853dc2464d82bf32cf3dee8121
Source dataset
uspto-grants-2001_03
Patent number
US06200981B1

Reaction notes

Loading…