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

HRID 1722894Notes

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

Workup

concentrationThe reaction mixture was concentrated under reduced pressure
additiona mixture of benzene and hexane (1:1 by volume)
additionwas added to the residue
customPrecipitated crystals
filtrationwere collected by filtration

Sources & evidence

ORD record: ord-0af2f1e91bf54132baa125c506d0d306
Source dataset: uspto-grants-1989_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04857650

Reaction notes

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