2-[(Naphthalen-1-yl)methylidene]butanedioic acid → 3-[(Naphthalen-1-yl)methylidene]oxolane-2,5-dione

HRID 1607394Notes

Reaction equation

HRID 1607394 reaction equation
[C:1]1([CH:11]=[C:12]([CH2:16][C:17]([OH:19])=[O:18])[C:13]([OH:15])=O)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1>C(OC(=O)C)(=O)C>[C:1]1([CH:11]=[C:12]2[CH2:16][C:17](=[O:18])[O:19][C:13]2=[O:15])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Participants

3

Reactant 1

HCID 541426892-[(Naphthalen-1-yl)methylidene]butanedioic acid

Product 1

HCID 543164283-[(Naphthalen-1-yl)methylidene]oxolane-2,5-dioneYield 48.1%

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Procedure

A mixture of 7.6 g of 2-(1-naphthylmethylene)succinic acid obtained and 130 ml of acetic anhydride was heated under reflux for 1 hour. The reaction mixture was concentrated under reduced pressure, and 50 ml of benzene was added to the residue. The precipitated crystals were collected by filtration to obtain 3.4 g of 2-(1-naphthylmethylene)succinic anhydride as orange yellow crystals.

Workup

  1. customobtained
  2. temperatureunder reflux for 1 hour
  3. concentrationThe reaction mixture was concentrated under reduced pressure, and 50 ml of benzene
  4. additionwas added to the residue
  5. filtrationThe precipitated crystals were collected by filtration

Sources & evidence

ORD record
ord-ea6366dbeeb34046810d7304d03bf657
Source dataset
uspto-grants-1989_09
Patent number
US04863904

Reaction notes

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