Benzoyl chloride → Methyl Benzoate

HRID 65128

Reaction equation

HRID 65128 reaction equation
C(Cl)(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:10](=O)([O:13][CH3:14])[O:11]C>[Br-].C([P+](CCCC)(CCCC)CCCC)CCC.S1(CCCC1)(=O)=O>[C:10]([O:13][CH3:14])(=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 7412Benzoyl chlorideHCID 12021Dimethyl Carbonate

Product 1

HCID 7150Methyl BenzoateYield 93%

Reagents, catalysts & solvents 2

HCID 76564Tetrabutylphosphonium bromideCatalystHCID 31347SulfolaneSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of 7.03 g (0.05 g mole) of benzoyl chloride, 4.5 g (0.05 g mole) of dimethyl carbonate, and 0.85 g (0.0025 g mole) of tetra-n-butyl phosphonium bromide (TBPB) in 25 ml of sulfolane was heated at 150° C. in a reaction flask equipped with reflux condenser. After 22 hours, the condenser was replaced by a distillation head and 6.3 g (93 percent yield) of methyl benzoate distilled at 83° C.-85° C./17 mm.

Workup

  1. customequipped
  2. temperaturewith reflux condenser

Sources & evidence

ORD record
ord-cd7c469e8ad042e59278ed20576ac749
Source dataset
uspto-grants-1986_09
Patent number
US04612386

Linked notes

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