Ethanol → HCID 20341477, compound

HRID 1395046Notes

Reaction equation

HRID 1395046 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([OH:10])[C:3]=1[CH:4]=O.[C:11]([O:17][CH2:18][CH3:19])(=[O:16])[CH2:12][C:13]([O-])=[O:14].C(O)C.N1CCCCC1>C(O)(=O)C>[Cl:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]2[C:3]=1[CH:4]=[C:12]([C:11]([O:17][CH2:18][CH3:19])=[O:16])[C:13](=[O:14])[O:10]2

Participants

6

Reactant 4

HCID 702EthanolHCID 8082PiperidineHCID 5283932-Chloro-6-hydroxybenzaldehydeHCID 3595298Propanedioic acid, monoethyl ester

Product 1

HCID 20341477HCID 20341477, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

15 g (0.0958 mole) of 2-chloro-6-hydroxy-benzaldehyde, 16.7 g (0.105 mole) ethyl malonate, 40 mL ethanol, 0.6 mL piperidine and 0.1 mL acetic acid are refluxed for 5 hours. After cooling the resultant product is dried. After drying, 14 g of ethyl 5-chlorocoumarin-3-carboxylate are obtained. (Yield=58%). Melting pointG =142°-144° C.

Workup

  1. customis dried
  2. customAfter drying

Sources & evidence

ORD record
ord-2c51f9e1474343b4a430918251857d7d
Source dataset
uspto-grants-1980_05
Patent number
US04201783

Reaction notes

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