Benzene → HCID 21883250, compound

HRID 328349Notes

Reaction equation

HRID 328349 reaction equation
[OH:1][C:2]1([CH3:21])[CH:9]2[C:10](=O)[C:5]([CH2:18][C:19]#[N:20])([C:6]3[CH:15]=[C:14]([O:16][CH3:17])[CH:13]=[CH:12][C:7]=3[CH2:8]2)[CH2:4][CH2:3]1.N1CCCC1.C1C=CC=CC=1.C([O-])(=O)C.[Na+]>O.C(O)(=O)C>[CH3:17][O:16][C:14]1[CH:15]=[C:6]2[C:7](=[CH:12][CH:13]=1)[CH2:8][CH2:9][C:10]1[C:5]2([CH2:18][C:19]#[N:20])[CH2:4][CH2:3][C:2](=[O:1])[CH:21]=1

Participants

7

Reactant 4

HCID 241BenzeneHCID 31268PyrrolidineHCID 517045Sodium AcetateHCID 54134001HCID 54134001, compound

Product 1

HCID 21883250HCID 21883250, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolvent2×HCID 962WaterSolvent2×

Procedure

A mixture of the ketol II (285 g., 1.00 mole), pyrrolidine (213 g., 3.0 mole), acetic acid (180 g., 3.0 mole) and benzene (2l) was refluxed with water separation (Dean-Stark trap) under nitrogen for 30 hours. A buffer solution of sodium acetate (285 g) in water (670 ml) and acetic acid (560 ml) was added and refluxing was continued for 24 hours. The mixture was cooled, washed with 3N sulphuric acid (2 × 500 ml) and work up to give the crude enone III (orange gum). A sample crystallized from methanol as pale yellow prisms; m.p. 133°-134° C.

Workup

  1. temperaturerefluxing
  2. temperatureThe mixture was cooled
  3. washwashed with 3N sulphuric acid (2 × 500 ml)

Sources & evidence

ORD record
ord-4022a02bb39c49baa0bc7cad9c6dc12a
Source dataset
uspto-grants-1977_04
Patent number
US04017497

Reaction notes

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