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

HRID 1751119Notes

Reaction equation

HRID 1751119 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-041bb98050dc474ab9b59cba2fd0cb15
Source dataset
uspto-grants-2015_10
Patent number
US09156840B2

Reaction notes

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