Diethyl Malonate → HCID 10496506, compound

HRID 2230258Notes

Reaction equation

HRID 2230258 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]=1[CH:13]=O.[C:15]([O:23][CH2:24][CH3:25])(=[O:22])[CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18].N1CCCCC1>C1C=CC=CC=1.C1(C)C=CC=CC=1>[CH2:20]([O:19][C:17](=[O:18])[C:16](=[CH:13][C:4]1[C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH:11]=[CH:12][C:3]=1[O:2][CH3:1])[C:15]([O:23][CH2:24][CH3:25])=[O:22])[CH3:21]

Participants

6

Reactant 3

HCID 7761Diethyl MalonateHCID 8082Piperidine2×HCID 793522-Methoxy-1-naphthaldehyde

Product 1

HCID 10496506HCID 10496506, compound

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 1140TolueneSolvent

Procedure

2-Methoxy-1-naphthaldehyde (25 g, 1.34.10−1 mol) in benzene (200 ml) is heated for 20 hours at reflux in the presence of diethyl malonate (25 ml, 1.65.10−1 mol, 1.23 eq.) and piperidine (2 ml, 2.02.10−2 mol, 0.15 eq.) in a Dean-Stark apparatus. After adding a few additional drops of piperidine, the mixture is returned to reflux for 20 hours. The reaction mixture is diluted with toluene (200 ml) and washed with water (125 ml). After separation of the phases, the organic phase is treated with a 1N hydrochloric acid solution (190 ml), then with a saturated NaHCO3 solution (125 ml) and with a saturated NaCl solution (125 ml). After drying over MgSO4 and evaporation under reduced pressure, the oil obtained is recrystallised from cyclohexane.

Workup

  1. temperatureto reflux for 20 hours
  2. washwashed with water (125 ml)
  3. customAfter separation of the phases
  4. additionthe organic phase is treated with a 1N hydrochloric acid solution (190 ml)
  5. dry with materialAfter drying over MgSO4 and evaporation under reduced pressure
  6. customthe oil obtained
  7. customis recrystallised from cyclohexane

Sources & evidence

ORD record
ord-9fb8d026feee4a8d8f5c325fa9677793
Source dataset
uspto-grants-2002_07
Patent number
US06423870B1

Reaction notes

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