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

HRID 1722180Notes

Reaction equation

HRID 1722180 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 70.2%

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Procedure

A mixture of 24.5 g of the 2-(1-naphthylmethylene)succinic acid obtained and 260 ml of acetic anhydride was heated for 60 minutes at 60° C. The reaction mixture was evaporated under reduced pressure, and to the residue was added a mixture of benzene and hexane (1:1). Precipitated crystals were collected by filtration to obtain 16.0 g of 2-(1-naphthylmethylene)succinic anhydride as orange yellow crystals.

Workup

  1. customobtained
  2. customThe reaction mixture was evaporated under reduced pressure
  3. additionto the residue was added
  4. additiona mixture of benzene and hexane (1:1)
  5. customPrecipitated crystals
  6. filtrationwere collected by filtration

Sources & evidence

ORD record
ord-7588cc9358094d0db8579e10a5532518
Source dataset
uspto-grants-1989_08
Patent number
US04853463

Reaction notes

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