Methanol → 3-Methoxycarbonyl-2-(1-naphthylmethylene)propionic acid

HRID 1722906Notes

Reaction equation

HRID 1722906 reaction equation
[C:1]1([CH:11]=[C:12]2[CH2:17][C:16](=[O:18])[O:15][C:13]2=[O:14])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[CH3:19][OH:20]>ClCCl>[CH3:19][O:20][C:16]([CH2:17][C:12](=[CH:11][C:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1)[C:13]([OH:15])=[O:14])=[O:18]

Participants

4

Reactant 2

HCID 887MethanolHCID 543164283-[(Naphthalen-1-yl)methylidene]oxolane-2,5-dione

Product 1

HCID 543827543-Methoxycarbonyl-2-(1-naphthylmethylene)propionic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 300 mg of 2-(1-naphthylmethylene)succinic anhydride and 18 ml of methyl alcohol in 30 ml of dry dichloromethane was heated under reflux for 5 hours. The reaction mixture was washed successively with a diluted hydrochloric acid and water, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to obtain 336 mg of 3-methoxycarbonyl-2-(1-naphthylmethylene)propionic acid as a white powder.

Workup

  1. temperatureunder reflux for 5 hours
  2. washThe reaction mixture was washed successively with a diluted hydrochloric acid and water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-7c6f993985394140a48f50b225fe1c61
Source dataset
uspto-grants-1989_08
Patent number
US04857650

Reaction notes

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