Benzene → HCID 12902869, compound

HRID 128091Notes

Reaction equation

HRID 128091 reaction equation
[O-]CC.[Na+].[OH:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH:17]=[CH:16][C:15]([CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:14][CH:13]=2)=[CH:8][CH:7]=1.C1C=CC=CC=1.Cl[CH:31]([C:37]([CH3:39])=O)[C:32]([O:34][CH2:35][CH3:36])=[O:33]>C(Cl)(Cl)(Cl)Cl>[CH2:35]([O:34][C:32]([C:31]1[O:5][C:6]2[CH:7]=[CH:8][C:9]([C:12]3[CH:17]=[CH:16][C:15]([CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:14][CH:13]=3)=[CH:10][C:11]=2[C:37]=1[CH3:39])=[O:33])[CH3:36]

Participants

6

Reactant 4

HCID 241BenzeneHCID 11858Ethyl 2-chloroacetoacetateHCID 2723922Sodium ethoxideHCID 23455887HCID 23455887, compound

Product 1

HCID 12902869HCID 12902869, compound

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

To a solution of 0.25 mole of sodium ethoxide is added 64 g. (0.25 mole) of ethyl 4-(4-hydroxyphenyl)phenylacetate. After stirring two hours the solution is evaporated, benzene is added, and the solution is further evaporated. The residue is dissolved in 800 ml. of benzene, 0.25 mole of ethyl α-chloroacetoacetate is added, and the mixture is stirred at room temperature, then heated at its reflux temperature for 16 hours and filtered hot. Evaporation provides a residue which is dissolved in carbon tetrachloride and filtered through silica gel. This intermediate is treated with concentrated sulfuric acid at 0° C. After stirring one hour, ice is added and the mixture is extracted with benzene. The benzene layer is dried, then evaporated. The residue is recrystallized from a dichloromethane-hexane mixture, then carbon tetrachloride, to provide ethyl 4-(2-ethoxycarbonyl 3-methylbenzofuran-5-yl)phenylacetate, m.p. 110°-112° C.

Workup

  1. customis evaporated
  2. additionbenzene is added
  3. customthe solution is further evaporated
  4. dissolutionThe residue is dissolved in 800 ml
  5. stirringthe mixture is stirred at room temperature
  6. temperatureheated at its
  7. temperaturereflux temperature for 16 hours
  8. filtrationfiltered hot
  9. customEvaporation
  10. customprovides a residue which
  11. filtrationfiltered through silica gel
  12. additionThis intermediate is treated with concentrated sulfuric acid at 0° C
  13. stirringAfter stirring one hour
  14. additionice is added
  15. extractionthe mixture is extracted with benzene
  16. dry with materialThe benzene layer is dried
  17. customevaporated
  18. customThe residue is recrystallized from a dichloromethane-hexane mixture

Sources & evidence

ORD record
ord-f840bd2a9e074b80ba8f4cddc1a444f2
Source dataset
uspto-grants-1981_03
Patent number
US04258213

Reaction notes

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