Methyl 4-[7-formylnaphth-1-ylmethyl]-3-methoxybenzoate → Methyl 4-(7-carboxynaphth-1-ylmethyl)-3-methoxybenzoate

HRID 2371797Notes

Reaction equation

HRID 2371797 reaction equation
CC(C)=[O:3].OS(O)(=O)=O.O=[Cr](=O)=O.[CH:14]([C:16]1[CH:25]=[C:24]2[C:19]([CH:20]=[CH:21][CH:22]=[C:23]2[CH2:26][C:27]2[CH:36]=[CH:35][C:30]([C:31]([O:33][CH3:34])=[O:32])=[CH:29][C:28]=2[O:37][CH3:38])=[CH:18][CH:17]=1)=[O:15]>CN(C)C=O>[C:14]([C:16]1[CH:25]=[C:24]2[C:19]([CH:20]=[CH:21][CH:22]=[C:23]2[CH2:26][C:27]2[CH:36]=[CH:35][C:30]([C:31]([O:33][CH3:34])=[O:32])=[CH:29][C:28]=2[O:37][CH3:38])=[CH:18][CH:17]=1)([OH:3])=[O:15]

Participants

4

Reactant 2

HCID 19906378Methyl 4-[7-formylnaphth-1-ylmethyl]-3-methoxybenzoateHCID 131709961Jones' reagent

Product 1

HCID 19906397Methyl 4-(7-carboxynaphth-1-ylmethyl)-3-methoxybenzoateYield 81%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of Jones reagent (1.53 ml) [prepared from 26.72 g chromium trioxide in 23 ml concentrated sulfuric acid, diluted with water to 100 ml] was added to a solution of methyl 4-(7-formylnaphth-1-yl-methyl)-3-methoxybenzoate (409 mg) in dimethylformamide (12 ml, distilled over CaH2). The mixture was stirred for 1 h and was partitioned between methylene chloride and 1N HCl. The organic layer was washed (1N HCl (twice), brine), dried (MgSO4) and evaporated. The residue was triturated with ether, ground to a powder and vacuum dried at 120° C. for 12 h to afford methyl 4-(7-carboxynaphth-1-ylmethyl)-3-methoxybenzoate (347 mg, 81%) as a pale yellow solid; mp 229.0°-230° C.; MS(CI), m/e=351(M+H).

Workup

  1. customwas partitioned between methylene chloride and 1N HCl
  2. washThe organic layer was washed (1N HCl (twice), brine),
  3. dry with materialdried (MgSO4)
  4. customevaporated
  5. customThe residue was triturated with ether, ground to a powder and vacuum
  6. customdried at 120° C. for 12 h

Sources & evidence

ORD record
ord-2582486fc46f4007b08a346862848a38
Source dataset
uspto-grants-1992_03
Patent number
US05095038

Reaction notes

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