Benzyl Chloride → Methyl 2,3-bis(benzyloxy)benzoate

HRID 2271362Notes

Reaction equation

HRID 2271362 reaction equation
[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([OH:10])[C:5]=1[OH:11].[CH2:13](Cl)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>>[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([O:10][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:5]=1[O:11][CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

3

Reactant 2

HCID 7503Benzyl ChlorideHCID 75484Methyl 2,3-Dihydroxybenzoate

Product 1

HCID 10665397Methyl 2,3-bis(benzyloxy)benzoate

Procedure

In one embodiment, the compounds can be prepared as shown in Scheme II. A dihydroxy benzoic acid methyl ester is reacted with benzyl chloride, to produce a Bis-benzyloxy benzoic acid methyl ester (1). The Bis-benzyloxy benzoic acid methyl ester can then be heated with LiOH to give a Bis-benzyloxy benzoic acid (2). The Bis-benzyloxy benzoic acid (2) is then reacted with an aminophenyl to produce a phenyl-benzamide (3). The phenyl-benzamide (3) is then reacted with hydrazine to give a triazol (4). The hydroxy groups can then be unprotecxted in the presence of palladium on charcoal to give the final product.

Workup

  1. customIn one embodiment, the compounds can be prepared

Sources & evidence

ORD record
ord-35b9123d442c44cab45dee25653e6b98
Source dataset
uspto-grants-2015_09
Patent number
US09120745B2

Reaction notes

Loading…