Sulfuric Acid → 6-(benzyloxy)-alpha-methyl-1H-benzotriazole-1-acetic acid

HRID 1109999Notes

Reaction equation

HRID 1109999 reaction equation
C[O:2][CH:3]([O:23]C)[CH:4]([CH3:22])[N:5]1[C:9]2[CH:10]=[C:11]([O:14][CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH:12]=[CH:13][C:8]=2[N:7]=[N:6]1.S(=O)(=O)(O)O>C(O)(=O)C.O>[CH2:15]([O:14][C:11]1[CH:12]=[CH:13][C:8]2[N:7]=[N:6][N:5]([CH:4]([CH3:22])[C:3]([OH:23])=[O:2])[C:9]=2[CH:10]=1)[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

5

Reactant 2

HCID 1118Sulfuric AcidHCID 190831276-(benzyloxy)-alpha-methyl-1H-benzotriazole-l-acetaldehyde dimethyl acetal

Product 1

HCID 545229956-(benzyloxy)-alpha-methyl-1H-benzotriazole-1-acetic acid

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

A solution of 6-(benzyloxy)-α-methyl-1H-benzotriazole-1-acetaldehyde dimethyl acetal (95 g, 0.272 mole) and concentrated sulfuric acid (20 ml) in acetic acid and water is heated at 72° C. for 20 hours, cooled to room temperature and concentrated in vacuo. The concentrated solution is diluted with acetone and water and treated with KMnO4 (140 g) in portions over a three hour period at 18°-30° C. with stirring.

Workup

  1. concentrationconcentrated in vacuo
  2. additionThe concentrated solution is diluted with acetone and water
  3. additiontreated with KMnO4 (140 g) in portions over a three hour period at 18°-30° C.

Sources & evidence

ORD record
ord-e5b4eb9fd041415c8844fabc00bfe28a
Source dataset
uspto-grants-1994_06
Patent number
US05324711

Reaction notes

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