Lithium hydroxide, monohydrate → 1-(4-Hydroxymethyl-benzyl)-1H-[1,2,3]triazole-4-carboxylic acid

HRID 928414Notes

Reaction equation

HRID 928414 reaction equation
C([O:3][C:4]([C:6]1[N:7]=[N:8][N:9]([CH2:11][C:12]2[CH:17]=[CH:16][C:15]([CH2:18][OH:19])=[CH:14][CH:13]=2)[CH:10]=1)=[O:5])C.O.[OH-].[Li+]>CO.O>[OH:19][CH2:18][C:15]1[CH:16]=[CH:17][C:12]([CH2:11][N:9]2[CH:10]=[C:6]([C:4]([OH:5])=[O:3])[N:7]=[N:8]2)=[CH:13][CH:14]=1

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 580812161-(4-Hydroxymethyl-benzyl)-1H-[1,2,3]triazole-4-carboxylic acid ethyl ester

Product 1

HCID 580813181-(4-Hydroxymethyl-benzyl)-1H-[1,2,3]triazole-4-carboxylic acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
30 °C

Procedure

A mixture of 1-(4-Hydroxymethyl-benzyl)-1H-[1,2,3]triazole-4-carboxylic acid ethyl ester (4.35 g, 9.42 mmol) and lithiumhydroxide-hydrate (1.976 g, 47.1 mmol) in 80 mL MeOH and 80 mL water was stirred at 30° C. for 3 h. The methanol was evaporated in vacuo. The residual aqueous layer was washed with ethyl acetate, acidified with 1 N aq. HCl and extracted with ethyl acetate. The organic layer was dried over MgSO4, filtered and evaporated to yield the crude product which was used in the next step without further purification. 1H-NMR (DMSO-d6, 400 MHz) 13.1 (broad s, 1H), 8.76 (s, 1H), 7.27-7.39 (m, 4H), 5.63 (s, 2H), 5.20 (t, 1H), 4.48 (d, 2H).

Workup

  1. customThe methanol was evaporated in vacuo
  2. washThe residual aqueous layer was washed with ethyl acetate
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organic layer was dried over MgSO4
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-3e89eaaad28e4999b3503dfa43834da5
Source dataset
uspto-grants-2016_03
Patent number
US09290485B2

Reaction notes

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