Bromoacetic Acid → Glycolic Acid

HRID 358971Notes

Reaction equation

HRID 358971 reaction equation
[H-].[Na+].[CH2:3]([N:10]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:12]([CH2:19][OH:20])=[N:11]1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.Br[CH2:22][C:23]([OH:25])=[O:24]>O1CCCC1>[CH2:3]([N:10]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:12]([CH2:19][OH:20])=[N:11]1)[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1.[C:23]([OH:25])(=[O:24])[CH2:22][OH:20]

Participants

6

Reactant 3

HCID 6227Bromoacetic AcidHCID 24758Sodium hydrideHCID 10657568(1-Benzylindazol-3-yl)methanol

Product 2

HCID 757Glycolic AcidHCID 10657568(1-Benzylindazol-3-yl)methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

2.4 g of sodium hydride (60% suspension in oil) are added to a solution of all the amount of 1-benzyl-3-hydroxymethylindazole obtained as described above, in 70 ml of tetrahydrofuran and the reaction mixture is heated to reflux under a stream of an inert gas (nitrogen). A solution of 3.5 g of bromoacetic acid in 40 ml of tetrahydrofuran is then added and the reaction mixture is refluxed for 90 minutes. After cooling, the reaction mixture is worked out in a standard manner and acidified. The resulting product is recrystallized from isopropanol. The ether of 1-benzyl-3-hydroxymethylindazole with glycolic acid is thus obtained (Compound I, R=R'=R"'=H), m.p. 136°-138° C.

Workup

  1. customobtained
  2. temperaturethe reaction mixture is heated
  3. temperatureto reflux under a stream of an inert gas (nitrogen)
  4. temperaturethe reaction mixture is refluxed for 90 minutes
  5. temperatureAfter cooling
  6. customThe resulting product is recrystallized from isopropanol

Sources & evidence

ORD record
ord-44723523324b43b0925f467831e1fcd4
Source dataset
uspto-grants-1991_03
Patent number
US04999367

Reaction notes

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