Chloromethyl Methyl Ether → HCID 18184922, compound

HRID 1358577Notes

Reaction equation

HRID 1358577 reaction equation
[H-].[Na+].C([O:9][C:10]1[CH:15]=[C:14]([CH3:16])[C:13]([OH:17])=[C:12]([CH3:18])[C:11]=1[CH3:19])(=O)C(C)(C)C.[CH3:20][O:21][CH2:22]Cl>O1CCCC1>[CH3:20][O:21][CH2:22][O:17][C:13]1[C:14]([CH3:16])=[CH:15][C:10]([OH:9])=[C:11]([CH3:19])[C:12]=1[CH3:18]

Participants

5

Reactant 3

HCID 7864Chloromethyl Methyl EtherHCID 24758Sodium hydrideHCID 149309244-Hydroxy-2,3,5-trimethylphenyl 2,2-dimethylpropanoate

Product 1

HCID 18184922HCID 18184922, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Sodium hydride (8.51 g, 55% suspension in mineral oil) was added to a solution of 4-hydroxy-2,3,5-trimethylphenol pivalate (35.4 g) in tetrahydrofuran (300 ml) at room temperature. The mixture was stirred for 30 minutes. To the reaction mixture was added dropwise methoxymethyl chloride (15.7 g). This mixture was stirred at room temperature for 1 hour. The solvent of the reaction mixture was evaporated under reduced pressure. The residue was partitioned between ethyl acetate and water. The organic extract was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was dissolved in methanol (100 ml) and to this solution was added dropwise a solution of potassium hydroxide (16.8 g) in methanol (100 ml). The mixture was stirred at room temperature and concentrated under reduced pressure. The residue was neutralized with 3N hydrochloric acid and extracted with ethyl acetate. The extract was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was chromatographed on a silica gel column using hexane:ethyl acetate=5:1 as the eluant to afford the title compound (27.5 g, Rf=0.16: thin layer chromatography on a silica gel plate using hexane:ethyl acetate=4:1 as the eluant).

Workup

  1. stirringThis mixture was stirred at room temperature for 1 hour
  2. customThe solvent of the reaction mixture was evaporated under reduced pressure
  3. customThe residue was partitioned between ethyl acetate and water
  4. extractionThe organic extract
  5. dry with materialwas dried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. dissolutionThe residue was dissolved in methanol (100 ml) and to this solution
  8. additionwas added dropwise a solution of potassium hydroxide (16.8 g) in methanol (100 ml)
  9. stirringThe mixture was stirred at room temperature
  10. concentrationconcentrated under reduced pressure
  11. extractionextracted with ethyl acetate
  12. dry with materialThe extract was dried over anhydrous sodium sulfate
  13. concentrationconcentrated under reduced pressure
  14. customThe residue was chromatographed on a silica gel column

Sources & evidence

ORD record
ord-3d6b961ee8d649d798c23cca69df6472
Source dataset
uspto-grants-2003_07
Patent number
US06596751B2

Reaction notes

Loading…