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

HRID 986355Notes

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

Conditions

Temperature: 60 °C

Procedure

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

Workup

customthe reaction mixture was evaporated under reduced pressure
additionTo the residue was added
additiona mixture of benzene and hexane (1/1, by volume)
filtrationThe precipitated crystals were collected by filtration

Sources & evidence

ORD record: ord-925941315bb24705bd64385d2b4ebc86
Source dataset: uspto-grants-1987_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04711958

Reaction notes

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