Diethyl Carbonate → Ethyl p-toluate

HRID 65129

Reaction equation

HRID 65129 reaction equation
[C:1]1([CH3:8])[CH:6]=[CH:5][C:4](Cl)=[CH:3][CH:2]=1.[C:9](=O)([O:13]CC)[O:10][CH2:11][CH3:12]>S1(CCCC1)(=O)=O.CC1C(CN2CCC(N3CCC(N4C(=O)NC5C4=CC=CC=5)CC3)CC2)=CC=CC=1>[C:1]1([CH3:8])[CH:6]=[CH:5][C:4]([C:9]([O:10][CH2:11][CH3:12])=[O:13])=[CH:3][CH:2]=1

Participants

5

Reactant 2

HCID 7766Diethyl CarbonateHCID 78104-Chlorotoluene

Product 1

HCID 66743Ethyl p-toluateYield 78%

Reagents, catalysts & solvents 2

HCID 10092649TbpbCatalystHCID 31347SulfolaneSolvent

Conditions

Temperature
170 °C

Procedure

A mixture of 7.73 g of p-toluyl chloride, 5.91 g of diethyl carbonate, and 0.85 g of TBPB in 25 ml of sulfolane was heated at 170° C. under reflux. After 44 hours, the reaction mixture was added to 200 g of crushed ice and this was extracted twice with 25-ml portions of hexane. The combined extracts were dried over anhydrous Na2SO4 and distilled to obtain 6.4 g (78 percent yield) of ethyl p-toluate, b.p. 120°-1° C./20 mm.

Workup

  1. temperatureunder reflux
  2. extractionthis was extracted twice with 25-ml portions of hexane
  3. dry with materialThe combined extracts were dried over anhydrous Na2SO4
  4. distillationdistilled

Sources & evidence

ORD record
ord-89c4edfe301549e2a78b54d2663f85b5
Source dataset
uspto-grants-1986_09
Patent number
US04612386

Linked notes

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