Ethyl levulinate → HCID 13920736, compound

HRID 868372Notes

Reaction equation

HRID 868372 reaction equation
[CH3:1][CH2:2][CH2:3][C:4]1[C:9]([OH:10])=[C:8]([C:11]([CH3:13])=[O:12])[CH:7]=[CH:6][C:5]=1[OH:14].N1CCCC1.[C:20]([O:27][CH2:28][CH3:29])(=[O:26])[CH2:21][CH2:22][C:23]([CH3:25])=O>C1(C)C=CC=CC=1>[OH:14][C:5]1[CH:6]=[CH:7][C:8]2[C:11](=[O:12])[CH2:13][C:23]([CH2:22][CH2:21][C:20]([O:27][CH2:28][CH3:29])=[O:26])([CH3:25])[O:10][C:9]=2[C:4]=1[CH2:3][CH2:2][CH3:1]

Participants

5

Reactant 3

HCID 10883Ethyl levulinateHCID 31268Pyrrolidine2×HCID 27751982',4'-Dihydroxy-3'-propylacetophenone

Product 1

HCID 13920736HCID 13920736, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 58.0 g (0.299 mole) of 2,4-dihydroxy-3-propylacetophenone and 29.5 ml (0.36 mole) of pyrrolidine in 250 ml of toluene was heated to reflux for three hours under a Dean-Stark trap. After cooling the mixture, 68.2 ml (0.48 mole) of ethyl levulinate was added and the mixture was refluxed for two hours. An additional 10 ml (0.12 mole) of pyrrolidine was added and the mixture was refluxed overnight under a Dean-Stark trap.

Workup

  1. temperatureto reflux for three hours under a Dean-Stark trap
  2. additionwas added
  3. temperaturethe mixture was refluxed for two hours
  4. temperaturethe mixture was refluxed overnight under a Dean-Stark trap

Sources & evidence

ORD record
ord-d25b2af187f54e469c3d5b778f389c1c
Source dataset
uspto-grants-1988_10
Patent number
US04778903

Reaction notes

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