Water → 3-[5-(3-chlorophenyl)-2H-tetrazol-2-yl]butanoic acid

HRID 639828Notes

Reaction equation

HRID 639828 reaction equation
O.OS(O)(=O)=O.[Cl:7][C:8]1[CH:9]=[C:10]([C:14]2[N:15]=[N:16][N:17]([CH:19]([CH3:23])[CH2:20][CH2:21][OH:22])[N:18]=2)[CH:11]=[CH:12][CH:13]=1.CC([OH:27])C>CC(C)=O>[Cl:7][C:8]1[CH:9]=[C:10]([C:14]2[N:15]=[N:16][N:17]([CH:19]([CH3:23])[CH2:20][C:21]([OH:27])=[O:22])[N:18]=2)[CH:11]=[CH:12][CH:13]=1

Participants

6

Reactant 4

HCID 962WaterHCID 1118Sulfuric AcidHCID 3776IsopropanolHCID 684296013-[5-(3-chlorophenyl)-2H-tetrazol-2-yl]butan-1-ol

Product 1

HCID 684316183-[5-(3-chlorophenyl)-2H-tetrazol-2-yl]butanoic acidYield 100%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of CrO3 (0.46 g, 4.63 mmol), H2O (2.5 mL) and concentrated H2SO4 (0.46 mL) was added to a solution of 3-[5-(3-chlorophenyl)-2H-tetrazol-2-yl]butan-1-ol (0.9 g, 3.6 mmol) in acetone (30 mL) at 0° C. The reaction was stirred at r.t. for 1.5 h. 2-Propanol was added and the mixture was concentrated. Sat. NaCl (25 mL) and EtOAc (50 mL) were added to the residue and the mixture was extracted. The water phase was re-extracted with EtOAc (50 mL) and the combined organic phases were dried (MgSO4) and concentrated to give 0.95 g (100%) of the title compound.

Workup

  1. concentrationthe mixture was concentrated
  2. additionSat. NaCl (25 mL) and EtOAc (50 mL) were added to the residue
  3. extractionthe mixture was extracted
  4. extractionThe water phase was re-extracted with EtOAc (50 mL)
  5. dry with materialthe combined organic phases were dried (MgSO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-ea7226872a9e4c4b802a45a8835aaf68
Source dataset
uspto-grants-2010_04
Patent number
US07691892B2

Reaction notes

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