Methanol → HCID 54750043, compound

HRID 328157Notes

Reaction equation

HRID 328157 reaction equation
C[O:2][C:3]1[CH:4]([C:15]([O:17][CH3:18])=[O:16])[C:5]2[C:10]([CH2:11][CH:12]=1)=[CH:9][CH:8]=[C:7]([O:13][CH3:14])[CH:6]=2.C(O)(=O)C(O)=O.CO>O>[OH:2][C:3]1[CH2:12][CH2:11][C:10]2[C:5](=[CH:6][C:7]([O:13][CH3:14])=[CH:8][CH:9]=2)[C:4]=1[C:15]([O:17][CH3:18])=[O:16]

Participants

5

Reactant 3

HCID 887MethanolHCID 971Oxalic AcidHCID 122399191-Naphthalenecarboxylic acid, 1,4-dihydro-2,7-dimethoxy-, methyl ester

Product 1

HCID 54750043HCID 54750043, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
20 °C

Procedure

A mixture of II (0.124 mole), oxalic acid (0.124 mole), 400 ml. methanol and 120 ml. water was warmed until solution occurred. This solution was then stirred at 20° C. for 18 hours. The resultant mixture was warmed again to solution and then concentrated. The residue was treated with dilute potassium carbonate and extracted with methylene chloride. The extracts were dried (MgSO4), filtered and concentrated to give III (~100%). Two recrystallizations of a small sample from methanol gave an analytical sample; mp 48.0°-48.5° C.

Workup

  1. concentrationconcentrated
  2. additionThe residue was treated with dilute potassium carbonate
  3. extractionextracted with methylene chloride
  4. dry with materialThe extracts were dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-a854c46023864a2ca41d5c9fdaa9b7fe
Source dataset
uspto-grants-1977_04
Patent number
US04016167

Reaction notes

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