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

HRID 1905310Notes

Reaction equation

HRID 1905310 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

To 260 ml of acetic anhydride was added 15.20 g of 2-(1-naphthylmethylene)succinic acid, and the mixture was heated under reflux for 1 hour. The reaction mixture was evaporated under reduced pressure, and 100 ml of dry benzene was added to the residue. The precipitated crystals were collected by filtration to obtain 6.80 g of 2-(1-naphthylmethylene)succinic anhydride as orange yellow crystals.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 1 hour
  3. customThe reaction mixture was evaporated under reduced pressure, and 100 ml of dry benzene
  4. additionwas added to the residue
  5. filtrationThe precipitated crystals were collected by filtration

Sources & evidence

ORD record
ord-aef5bb294bb34c08af002acbb794ed33
Source dataset
uspto-grants-1989_06
Patent number
US04841067

Reaction notes

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