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

HRID 2270866Notes

Reaction equation

HRID 2270866 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-0fbe7863cb7e451087e885d04432da1b
Source dataset
uspto-grants-2001_12
Patent number
US06331640B1

Reaction notes

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