Ethyl (3-Hydroxyphenyl)acetate → Ethyl 3[(2-nitro-3-phenylbenzofuran-5-yl)methoxy]phenylacetate

HRID 614097Notes

Reaction equation

HRID 614097 reaction equation
[O-]CC.[Na+].[OH:5][C:6]1[CH:7]=[C:8]([CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH:9]=[CH:10][CH:11]=1.Br[CH2:19][C:20]1[CH:21]=[CH:22][C:23]2[O:27][C:26]([N+:28]([O-:30])=[O:29])=[C:25]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[C:24]=2[CH:37]=1>C(O)C>[N+:28]([C:26]1[O:27][C:23]2[CH:22]=[CH:21][C:20]([CH2:19][O:5][C:6]3[CH:7]=[C:8]([CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH:9]=[CH:10][CH:11]=3)=[CH:37][C:24]=2[C:25]=1[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)([O-:30])=[O:29]

Participants

5

Reactant 3

HCID 572437Ethyl (3-Hydroxyphenyl)acetateHCID 2723922Sodium ethoxideHCID 13531604HCID 13531604, compound

Product 1

HCID 20333822Ethyl 3[(2-nitro-3-phenylbenzofuran-5-yl)methoxy]phenylacetate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 0.0066 ml. of sodium ethoxide in 50 ml. of ethanol is added 1.2 g. (0.0066 mole) of ethyl 3-hydroxyphenylacetate. The mixture is heated at its reflux temperature for three hours, then 2 g. (0.006 mole) of 5-bromomethyl-2-nitro-3-phenylbenzofuran is added. The mixture is heated at its reflux temperature for 16 hours. On cooling of the reaction mixture a yellow precipitate is obtained which is separated by filtration. Recrystallization from a mixture of hexane and benzene provides ethyl 3[(2-nitro-3-phenylbenzofuran-5-yl)methoxy]phenylacetate, m.p. 67°-68° C.

Workup

  1. temperatureThe mixture is heated at its
  2. temperaturereflux temperature for three hours
  3. temperatureThe mixture is heated at its
  4. temperaturereflux temperature for 16 hours
  5. temperatureOn cooling of the reaction mixture a yellow precipitate
  6. customis obtained which
  7. customis separated by filtration
  8. customRecrystallization
  9. additionfrom a mixture of hexane and benzene

Sources & evidence

ORD record
ord-dd1327e4cf284c2393352acf37b51bc9
Source dataset
uspto-grants-1979_03
Patent number
US04143154

Reaction notes

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