Formaldehyde → HCID 68871722, compound

HRID 1260908Notes

Reaction equation

HRID 1260908 reaction equation
[H-].[Na+].[C:3](OCC)(=O)C(OCC)=O.[Cl:13][C:14]1[CH:15]=[C:16]([CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23])[CH:17]=[CH:18][C:19]=1[Cl:20].C=O.C(=O)([O-])[O-].[K+].[K+]>C1(C)C=CC=C(C)C=1.C(O)C>[Cl:13][C:14]1[CH:15]=[C:16]([C:21](=[CH2:3])[C:22]([O:24][CH2:25][CH3:26])=[O:23])[CH:17]=[CH:18][C:19]=1[Cl:20]

Participants

8

Reactant 5

HCID 712FormaldehydeHCID 7268Diethyl OxalateHCID 11430Potassium CarbonateHCID 24758Sodium hydrideHCID 2737422Ethyl 3,4-dichlorophenylacetate

Product 1

HCID 68871722HCID 68871722, compoundYield 71%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 7929M-XyleneSolvent2×

Procedure

To a solution of sodium hydride (60% in oil, 6.56 g) in m-xylene (100 mL) was slowly added ethanol (15.7 mL) at 0° C. and then diethyl oxalate (32.0 g) was added. Furthermore, a solution of ethyl 3,4-dichlorophenylacetate (51.0 g) in m-xylene (30 mL) was added at 0° C., and the mixture was stirred at room temperature for 14 hr. To the reaction mixture was added 37% aqueous formalin solution (140 mL) at room temperature, and the mixture was stirred at room temperature for 1 hr. Furthermore, potassium carbonate (115 g) was added at room temperature, and the mixture was stirred at room temperature for 1 hr. The insoluble material was filtered off, and the filtrate was partitioned between ethyl acetate (500 mL) and water (500 mL). The organic layer was separated, washed with brine and dried, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (solvent; 5% ethyl acetate/hexane) to give crude ethyl 2-(3,4-dichlorophenyl)acrylate (38.1 g, 44%) as a colorless oil.

Workup

  1. customat 0° C.
  2. stirringthe mixture was stirred at room temperature for 1 hr
  3. stirringthe mixture was stirred at room temperature for 1 hr
  4. filtrationThe insoluble material was filtered off
  5. customthe filtrate was partitioned between ethyl acetate (500 mL) and water (500 mL)
  6. customThe organic layer was separated
  7. washwashed with brine
  8. customdried
  9. customthe solvent was evaporated under reduced pressure
  10. customThe obtained residue was purified by silica gel column chromatography (solvent; 5% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-11372bb424614079a4c3aaf91b641a85
Source dataset
uspto-grants-2013_06
Patent number
US08470816B2

Reaction notes

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