Phthalide → HCID 20369812, compound

HRID 616354Notes

Reaction equation

HRID 616354 reaction equation
[H-].[Na+].[CH:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[CH:5][C:4]=1[OH:13].[H][H].[C:16]1([C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH2:19][O:18]1)=[O:17]>CN(C)C=O>[C:16]([C:25]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[CH2:19][O:13][C:4]1[CH:5]=[CH:6][C:7]2[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH:3]=1)([OH:18])=[O:17]

Participants

6

Reactant 4

HCID 6885PhthalideHCID 86632-NaphtholHCID 24758Sodium hydrideHCID 178418361HCID 178418361, compound

Product 1

HCID 20369812HCID 20369812, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

To a stirred suspension of 9.6 g. (0.2 mole) of a 50% dispersion of sodium hydride in mineral oil in 60 ml. of dimethylformamide is added dropwise a solution of 28.8 g. (0.2 mole) of 2-naphthol in 100 ml. of dimethylformamide at such a rate that the temperature does not exceed 25° C. After hydrogen evolution is complete, 26.8 g. (0.2 mole) of phthalide in 100 ml. of dimethylformamide is added dropwise and the stirred mixture is heated under reflux for 2 hours. The solvent is distilled off and the residue is diluted with ice-water. The mixture is extracted with ether and then the aqueous portion is made acidic with 12 N hydrochloric acid. The crystalline precipitate is filtered and recrystallized from aqueous ethanol, using decolorizing carbon to give 2-(2-carboxybenzyloxy)naphthalene.

Workup

  1. additionTo a stirred suspension of 9.6 g
  2. customdoes not exceed 25° C
  3. temperaturethe stirred mixture is heated
  4. temperatureunder reflux for 2 hours
  5. distillationThe solvent is distilled off
  6. additionthe residue is diluted with ice-water
  7. extractionThe mixture is extracted with ether
  8. filtrationThe crystalline precipitate is filtered
  9. customrecrystallized from aqueous ethanol

Sources & evidence

ORD record
ord-f0446d22bc3e4d92b4fdc2db54c8cd55
Source dataset
uspto-grants-1978_02
Patent number
US04073912

Reaction notes

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