4-Methylbenzoyl Chloride → 1,1-Dimethylethyl 4-methylbenzoate

HRID 2363050Notes

Reaction equation

HRID 2363050 reaction equation
[CH3:1][C:2]([CH3:5])([O-:4])[CH3:3].[Li+].[C:7]1([CH3:16])[CH:12]=[CH:11][C:10]([C:13](Cl)=[O:14])=[CH:9][CH:8]=1>O1CCCC1.O>[CH3:16][C:7]1[CH:12]=[CH:11][C:10]([C:13]([O:4][C:2]([CH3:5])([CH3:3])[CH3:1])=[O:14])=[CH:9][CH:8]=1

Participants

5

Reactant 2

HCID 134054-Methylbenzoyl ChlorideHCID 236647642-Propanol, 2-methyl-, lithium salt (1:1)

Product 1

HCID 116297491,1-Dimethylethyl 4-methylbenzoate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Lithium tert-butoxide (1M in hexanes, 178 mL, 0.178 mol) was added dropwise at room temperature to p-toluoyl chloride (25 g, 0.162 mol) in tetrahydrofuran (150 mL). The mixture was stirred at room temperature overnight and then diluted with water and extracted with ethyl acetate. The extract was washed with brine, dried (MgSO4), and evaporated to give product as an oil which crystallized on standing (31 g, 98%)

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with brine
  3. dry with materialdried (MgSO4)
  4. customevaporated
  5. customto give product as an oil which
  6. customcrystallized

Sources & evidence

ORD record
ord-1ef67022019743248df59102ba1b3f2a
Source dataset
uspto-grants-2014_04
Patent number
US08691836B2

Reaction notes

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