Lithium hydroxide, monohydrate → 4-(Azidomethyl)-2-chlorobenzoic acid

HRID 393100Notes

Reaction equation

HRID 393100 reaction equation
O.[OH-].[Li+].[N:4]([CH2:7][C:8]1[CH:17]=[CH:16][C:11]([C:12]([O:14]C)=[O:13])=[C:10]([Cl:18])[CH:9]=1)=[N+:5]=[N-:6]>O.O1CCCC1>[N:4]([CH2:7][C:8]1[CH:17]=[CH:16][C:11]([C:12]([OH:14])=[O:13])=[C:10]([Cl:18])[CH:9]=1)=[N+:5]=[N-:6]

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 57461226Methyl 4-(azidomethyl)-2-chlorobenzoate

Product 1

HCID 226614994-(Azidomethyl)-2-chlorobenzoic acidYield 60%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of lithium hydroxide monohydrate (7.00 g, 166.8 mmol) in water (100 mL) was added to a solution of 4-(azidomethyl)-2-chlorobenzoic acid, methyl ester (12.17 g, 53.9 mmol) in tetrahydrofuran (100 mL) and the resulting solution was stirred at room temperature overnight. The reaction mixture was concentrated to remove some of the tetrahydrofuran. The solution was extracted with ethyl acetate (200 mL) and the extract was discarded. Then 1 M HCl (100 mL) was added and the mixture was extracted with ethyl acetate (2×200 mL). The combined organic layers were dried (MgSO4), filtered, and evaporated to give 4-(azidomethyl)-2-chlorobenzoic acid (6.82 g, 60%) as a white solid, mp 87-88° C.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customto remove some of the tetrahydrofuran
  3. extractionThe solution was extracted with ethyl acetate (200 mL)
  4. additionThen 1 M HCl (100 mL) was added
  5. extractionthe mixture was extracted with ethyl acetate (2×200 mL)
  6. dry with materialThe combined organic layers were dried (MgSO4)
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-a5b3d172c037400c9763cf78e15fd065
Source dataset
uspto-grants-2004_10
Patent number
US06803384B2

Reaction notes

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