Benzoic Acid → 75369-57-2

HRID 1395628

Reaction equation

HRID 1395628 reaction equation
[C:1]([O:9][CH2:10][CH3:11])(=[O:8])[CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4].[Cl:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2[O:23][C:22]([CH:24]=O)=[CH:21][CH:20]=2)=[CH:15][CH:14]=1.C(O)(=O)C1C=CC=CC=1.N1CCCCC1>C1C=CC=CC=1.O>[Cl:12][C:13]1[CH:14]=[CH:15][C:16]([C:19]2[O:23][C:22]([CH:24]=[C:2]([C:3]([O:5][CH2:6][CH3:7])=[O:4])[C:1]([O:9][CH2:10][CH3:11])=[O:8])=[CH:21][CH:20]=2)=[CH:17][CH:18]=1

Participants

7

Reactant 4

HCID 243Benzoic AcidHCID 7761Diethyl MalonateHCID 8082PiperidineHCID 6761845-(4-Chlorophenyl)-2-furaldehyde

Product 1

HCID 213036575369-57-2

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 962WaterSolvent

Procedure

Diethyl malonate (88 g, 0.55 mole) and 5-(p-chlorophenyl)-2-furaldehyde (104 g, 0.50 mole) were placed in 1.0 liter of benzene containing benzoic acid (10 g) and piperidine (18 ml). The 2.0 liter flask was equipped with a Dean-Stark trap for water removal, and the mixture was refluxed for 4 hours on a steam bath. The mixture was concentrated to an oil under reduced pressure. Washing the residue with benzene (500 ml) yielded a dark solid which was recrystallized from cyclohexane yielding yellow product (111 g, 64% yeild), m.p. 78°-80°.

Workup

  1. temperaturethe mixture was refluxed for 4 hours on a steam bath
  2. concentrationThe mixture was concentrated to an oil under reduced pressure
  3. washWashing the residue with benzene (500 ml)
  4. customyielded a dark solid which
  5. customwas recrystallized from cyclohexane yielding yellow product (111 g, 64% yeild), m.p. 78°-80°

Sources & evidence

ORD record
ord-057a12e191964635997db80d6f6b0601
Source dataset
uspto-grants-1980_05
Patent number
US04205003

Linked notes

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