tert-Butanol → Tert-butyl 3-methylbenzoate

HRID 1531948Notes

Reaction equation

HRID 1531948 reaction equation
[C:1]([OH:5])([CH3:4])([CH3:3])[CH3:2].C([Li])CCC.[C:11]1([CH3:20])[CH:16]=[CH:15][CH:14]=[C:13]([C:17](Cl)=[O:18])[CH:12]=1>O1CCCC1>[CH3:20][C:11]1[CH:12]=[C:13]([CH:14]=[CH:15][CH:16]=1)[C:17]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:18]

Participants

5

Reactant 3

HCID 6386tert-ButanolHCID 743753-Methylbenzoyl chlorideHCID 178418339Butyllithium

Product 1

HCID 236097Tert-butyl 3-methylbenzoate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of tert-butanol (12.2 ml) in tetrahydrofuran (300 ml) at 0° C. was added n-butyllithium (52 ml) dropwise over 10 minutes. m-Toluoyl chloride (20 g) was added and the mixture heated at reflux for 1 hours. The mixture was partitioned between ethyl acetate and water and the organic phase dried (MgSO4) and evaporated. Purified by chromatography eluting with 20% dichloromethane in isohexane. Yield 14.78 g. Used directly in the next step.

Workup

  1. temperaturethe mixture heated
  2. temperatureat reflux for 1 hours
  3. customThe mixture was partitioned between ethyl acetate and water
  4. dry with materialthe organic phase dried (MgSO4)
  5. customevaporated
  6. customPurified by chromatography
  7. washeluting with 20% dichloromethane in isohexane

Sources & evidence

ORD record
ord-a3d21ae791f04fdb825dd8deaed361da
Source dataset
uspto-grants-2001_03
Patent number
US06200981B1

Reaction notes

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