Acetic Acid → 1-(2-Hydroxyethyl)-2,5-dimethylpyrrole

HRID 2298440Notes

Reaction equation

HRID 2298440 reaction equation
[NH2:1]C(O)C.[CH2:5]([CH2:9][C:10](=O)[CH3:11])[C:6]([CH3:8])=O.[C:13]([OH:16])(=O)[CH3:14].C1(C)C=CC=CC=1>C(OCC)(=O)C.O>[CH3:8][C:6]1[N:1]([CH2:14][CH2:13][OH:16])[C:10]([CH3:11])=[CH:9][CH:5]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 1140TolueneHCID 80352,5-HexanedioneHCID 522583Acetaldehyde ammonia

Product 1

HCID 959631-(2-Hydroxyethyl)-2,5-dimethylpyrrole

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

30.5 g (0.5 mol) of aminoethanol, 57 g (0.5 mol) of acetonylaceton and 0.35 g (5 mmol, a catalytic amount) of acetic acid were added to 300 ml of toluene, and then, the mixture was refluxed for 3 hours using a Dean-stark trap. The reaction mixture was cooled to room temperature, 200 ml of water and 100 ml of ethyl acetate were added thereto, and was stirred for 30 minutes. The organic phase was separated and filtered through a silica gel pad, and the filtrate was distilled under a reduced pressure to obtain 66 g of the titled compound in the form of a pale orange oil (yield: 95%).

Workup

  1. temperaturethe mixture was refluxed for 3 hours
  2. customThe organic phase was separated
  3. filtrationfiltered through a silica gel pad
  4. distillationthe filtrate was distilled under a reduced pressure

Sources & evidence

ORD record
ord-d33b5987186a43cbb2535f8fb2d8e15b
Source dataset
uspto-grants-2002_12
Patent number
US06492523B2

Reaction notes

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