Reaction #1583877

Reaction equation

methanol

2,2-diphenylacetic acid

oxalyl chloride

→

methyl 2,2-diphenylacetate

Yield 98.7%

Solvents

DMF

dichloromethane

dichloromethane

Conditions

Workup

1. 1
   Otherwas conducted at 25° C
2. 2
   OtherAfter the completion of reaction
3. 3
   Otherthe mixture was evaporated under reduced pressure
4. 4
   Otherto remove oxalyl chloride
5. 5
   Temperatureunder cooling in an ice bath respectively
6. 6
   Otherwas conducted at 25° C
7. 7
   OtherAfter the completion of reaction
8. 8
   Washthe reaction solution was washed with a saturated aqueous NaCl solution
9. 9
   DryingThe organic phase was dried over sodium sulfate
10. 10
    Filtrationfiltered by suction
11. 11
    OtherThe filtrate was evaporated to dryness

Procedure

To a 500 mL three-opening flask were added 2,2-diphenylacetic acid (20 g, 94 mmol) and 200 mL dichloromethane. After stirring, 1 mL DMF was added. To the mixture was slowly added oxalyl chloride (13.16 g, 104 mmol) dropwisely in an ice bath. The reaction was conducted at 25° C. After the completion of reaction, the mixture was evaporated under reduced pressure to remove oxalyl chloride. To the reaction flask were slowly added dichloromethane (100 mL) and anhydrous methanol (3.61 g, 113 mmol) dropwisely under cooling in an ice bath respectively. The reaction was conducted at 25° C. After the completion of reaction, the reaction solution was washed with a saturated aqueous NaCl solution. The organic phase was dried over sodium sulfate, and filtered by suction. The filtrate was evaporated to dryness to produce methyl 2,2-diphenylacetate (21 g) in a yield of 98.7%.

Source