Ethyl Acetoacetate → HCID 12333358, compound

HRID 974230Notes

Reaction equation

HRID 974230 reaction equation
[C:1]1(=[O:8])[CH2:6][CH2:5][CH2:4][C:3](=[O:7])[CH2:2]1.[C:9](OCC)(=[O:14])[CH2:10][C:11]([CH3:13])=O>N1C=CC=CC=1.CN(C)C1C=CN=CC=1>[CH3:13][C:11]1[C:2]2[C:1](=[O:8])[CH2:6][CH2:5][CH2:4][C:3]=2[O:7][C:9](=[O:14])[CH:10]=1

Participants

5

Reactant 2

HCID 8868Ethyl Acetoacetate2×HCID 104341,3-Cyclohexanedione

Product 1

HCID 12333358HCID 12333358, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Procedure

231.2 g (2.0 mol) of cyclohexan-1,3-dione (97%) are refluxed under nitrogen for 2.5 hours in 670 ml of absolute pyridine with 325.3 q (1.25×2.0 mol) of ethyl acetoacetate and 4.88 (0.02×2 mol) of 4-dimethylaminopyridine. Then 65.1 g (0.25×2.0 mol) of ethyl acetoacetate are again added and the mixture is boiled for a further 3 hours. The pyridine is then distilled off in vacuo and the oily residue is stirred while still warm with 100 ml of a mixture of cyclohexane/ethyl acetate (1:1). The reaction product which crystallises out is suction filtered and dried. Yield: 136.9 g (39.2% of theory) The mother liquor is freed from solvent in vacuo using a rotary evaporator and the oily residue is distilled in vacuo. The distillate solidifies into a white crystalline substance.

Workup

  1. distillationThe pyridine is then distilled off in vacuo
  2. temperaturewhile still warm with 100 ml of a mixture of cyclohexane/ethyl acetate (1:1)
  3. customThe reaction product which crystallises out is suction
  4. filtrationfiltered
  5. customdried
  6. customa rotary evaporator
  7. distillationthe oily residue is distilled in vacuo

Sources & evidence

ORD record
ord-6b36951f2c3a47b4a911274c2b7c3b2b
Source dataset
uspto-grants-1991_11
Patent number
US05068334

Reaction notes

Loading…