Oxalic Acid → HCID 11381931, compound

HRID 840029Notes

Reaction equation

HRID 840029 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[C:8]([CH:13]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH:7]=[CH:6]2.[H-].[Na+].CI.[C:28](O)(=O)C(O)=O>CO>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[C:8]([C:13]([CH3:28])([C:19]([O:21][CH2:22][CH3:23])=[O:20])[C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH:7]=[CH:6]2

Participants

6

Reactant 4

HCID 971Oxalic AcidHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 15688874Diethyl (6-methoxynaphthalen-2-yl)propanedioate

Product 1

HCID 11381931HCID 11381931, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 31.6 g. of diethyl 6-methoxy-2-naphthylmalonate, 2.4 g. of sodium hydride, and 350 ml. of methanol is stirred for one hour; then 24 g. of methyliodide are added and the resulting mixture is refluxed for 2 hours. The cooled mixture is neutralized with aqueous oxalic acid. The product, diethyl 6-methoxy-2-naphthyl-α-methylmalonate, is isolated, hydrolyzed, and decarboxylated by the means of the above described processes to give 6-methoxy-2-naphthyl-α-methylacetic acid.

Workup

  1. additionA mixture of 31.6 g
  2. temperaturethe resulting mixture is refluxed for 2 hours

Sources & evidence

ORD record
ord-228af057def14986968448e4154c34d5
Source dataset
uspto-grants-1978_06
Patent number
US04097674

Reaction notes

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