Sodium Hydroxide → HCID 21391794, compound

HRID 461707Notes

Reaction equation

HRID 461707 reaction equation
[CH3:1][C:2]([C:13]1[CH:18]=[CH:17][C:16]([C:19]([C:21]2[CH:30]=[CH:29][C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[CH:22]=2)=[O:20])=[CH:15][CH:14]=1)(C(OCC)=O)[C:3]([O:5]CC)=[O:4].[OH-].[Na+]>O>[CH:22]1[C:23]2[C:28](=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:29]=[CH:30][C:21]=1[C:19]([C:16]1[CH:17]=[CH:18][C:13]([CH:2]([CH3:1])[C:3]([OH:5])=[O:4])=[CH:14][CH:15]=1)=[O:20]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 21391781HCID 21391781, compound

Product 1

HCID 21391794HCID 21391794, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A mixture of 9.1 parts of diethyl 2-methyl-2-[p-(2-naphthoyl)phenyl]malonate, 6 parts of sodium hydroxide and 150 parts of water is stirred and refluxed for 8 hours. The reaction mixture is allowed to stand overnight at room temperature. The whole is diluted with water and the product is extracted with ether. The organic layer is separated and discarded. The aqueous phase is degassed on a rotavapor, filtered and acidified with hydrochloric acid solution: an oil is separated which solidifies on standing. The latter is extracted with ether and the extract is washed with water, dried and evaporated. The residue is crystallized from acetonitrile. The product is filtered off, washed with acetonitrile and dried, yielding p-(2-naphthoyl)hydratropic acid; mp. 149.7° C.

Workup

  1. temperaturerefluxed for 8 hours
  2. extractionthe product is extracted with ether
  3. customThe organic layer is separated
  4. customThe aqueous phase is degassed on a rotavapor
  5. filtrationfiltered
  6. customan oil is separated which
  7. extractionThe latter is extracted with ether
  8. washthe extract is washed with water
  9. customdried
  10. customevaporated
  11. customThe residue is crystallized from acetonitrile
  12. filtrationThe product is filtered off
  13. washwashed with acetonitrile
  14. customdried

Sources & evidence

ORD record
ord-d3e77b7c4e424102ba538bcc15ef6cca
Source dataset
uspto-grants-1977_12
Patent number
US04064132

Reaction notes

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