Sodium Hydroxide → (+/-)-5decyl-alpha-phenyl-2H-tetrazole-2-acetic acid

HRID 264069Notes

Reaction equation

HRID 264069 reaction equation
[OH-].[Na+].[CH2:3]([C:13]1[N:14]=[N:15][N:16]([CH:18]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:19]([O:21]CC)=[O:20])[N:17]=1)[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]>C(O)C>[CH2:3]([C:13]1[N:14]=[N:15][N:16]([CH:18]([C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)[C:19]([OH:21])=[O:20])[N:17]=1)[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 19391039ethyl (+/-)-5-decyl-alpha-phenyl-2H-tetrazole-2-acetate

Product 1

HCID 21469480(+/-)-5decyl-alpha-phenyl-2H-tetrazole-2-acetic acidYield 92%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Solid NaOH (0.33 g, 0.0084 mol) was added to a solution of ethyl (±)-5-decyl-α-phenyl-2H-tetrazole-2-acetate in 50 mL ethanol (90%). The resulting solution was stirred for 1 hour and concentrated in vacuo. The residue was partitioned between diethyl ether and water and the aqueous layer was acidified with 1N HCl. The acidified aqueous layer was extracted with diethyl ether and this ether layer was dried over MgSO4, filtered, and evaporated to give the title compound (1.78 g, 92%), mp 62°-64° C.

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue was partitioned between diethyl ether and water
  3. extractionThe acidified aqueous layer was extracted with diethyl ether
  4. dry with materialthis ether layer was dried over MgSO4
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-2e600908c0a54e4cb644272ae4cc84af
Source dataset
uspto-grants-1997_07
Patent number
US05646170

Reaction notes

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