Ethanol → HCID 12422088, compound

HRID 436161Notes

Reaction equation

HRID 436161 reaction equation
C(O)C.[C:4]([CH:6]1[C:15]2[CH:14]=[CH:13][CH:12]=[C:11]([C:16]([O:18]CC)=[O:17])[C:10]=2[CH2:9][CH2:8][CH2:7]1)#[N:5].[OH-].[Na+]>O>[C:4]([CH:6]1[C:15]2[CH:14]=[CH:13][CH:12]=[C:11]([C:16]([OH:18])=[O:17])[C:10]=2[CH2:9][CH2:8][CH2:7]1)#[N:5]

Participants

5

Reactant 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 12422087HCID 12422087, compound

Product 1

HCID 12422088HCID 12422088, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

In 90 ml. of ethanol is dissolved 9.6 g. of ethyl 1-cyano-1,2,3,4-tetrahydro-5-naphthoate and a solution of 2.5 g. of sodium hydroxide in 90 ml. of water is added. The mixture is stirred under heating at 50° C for 3 hours, after which the ethanol is distilled off. Then, following the addition of 2N hydrochloric acid, the residue is extracted with chloroform. The organic layer is washed with water and dried over anhydrous magnesium sulfate. The solvent is distilled off under reduced pressure and the crystalline residue is recrystallized from benzene. The described procedure gives 1-cyano-1,2,3,4-tetrahydro-5-naphthoic acid, melting point: 177°-179° C.

Workup

  1. distillationafter which the ethanol is distilled off
  2. additionthe addition of 2N hydrochloric acid
  3. extractionthe residue is extracted with chloroform
  4. washThe organic layer is washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationThe solvent is distilled off under reduced pressure
  7. customthe crystalline residue is recrystallized from benzene

Sources & evidence

ORD record
ord-eabfdfbaa0604c0db3406f9da28476da
Source dataset
uspto-grants-1977_02
Patent number
US04007225

Reaction notes

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