Hydroxyphenylacetic acid → HCID 20333831, compound

HRID 1706651Notes

Reaction equation

HRID 1706651 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=[O:10])=[CH:4][CH:3]=1.[OH-].[Na+].Br[CH2:15][C:16]1[CH:17]=[CH:18][C:19]2[O:23][C:22]([N+:24]([O-:26])=[O:25])=[C:21]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[C:20]=2[CH:33]=1>C(O)C>[N+:24]([C:22]1[O:23][C:19]2[CH:18]=[CH:17][C:16]([CH2:15][O:1][C:2]3[CH:3]=[CH:4][C:5]([CH2:8][C:9]([OH:11])=[O:10])=[CH:6][CH:7]=3)=[CH:33][C:20]=2[C:21]=1[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)([O-:26])=[O:25]

Participants

5

Reactant 3

HCID 127Hydroxyphenylacetic acidHCID 14798Sodium HydroxideHCID 13531604HCID 13531604, compound

Product 1

HCID 20333831HCID 20333831, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a mixture of 1 g. (0.0066 mole) of 4-hydroxyphenylacetic acid and 0.53 g. of sodium hydroxide in 100 ml. of ethanol is added 2 g. (0.006 mole) of 5-bromomethyl-2-nitro-3-phenylbenzofuran, and the mixture is heated at its reflux temperature for 16 hours. The reaction mixture is evaporated to provide a residue which is extracted thoroughly with chloroform. The residue is separated from chloroform and dissolved in water. The water is acidified to pH 3. The precipitate is separated by filtration, dissolved in dichloromethane, and the dichloromethane solution is dried. The dichloromethane solution is evaporated to provide a yellow solid which is recrystallized from ethanol to provide 4-[(2-nitro-3-phenylbenzofuran-5-yl)methoxy]phenylacetic acid, m.p. 179°-180° C.

Workup

  1. additionTo a mixture of 1 g
  2. temperaturereflux temperature for 16 hours
  3. customThe reaction mixture is evaporated
  4. customto provide a residue which
  5. extractionis extracted thoroughly with chloroform
  6. customThe residue is separated from chloroform
  7. dissolutiondissolved in water
  8. customThe precipitate is separated by filtration
  9. dissolutiondissolved in dichloromethane
  10. dry with materialthe dichloromethane solution is dried
  11. customThe dichloromethane solution is evaporated
  12. customto provide a yellow solid which
  13. customis recrystallized from ethanol

Sources & evidence

ORD record
ord-4ae6fc2b80e14bc39738e6ce3986ff6e
Source dataset
uspto-grants-1980_06
Patent number
US04208335

Reaction notes

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