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

HRID 1030200Notes

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 38 g of (1-naphthalenylmethylene)butanedioic acid and 270 ml of acetic anhydride was heated at 60° C. for one hour. The mixture was evaporated under reduced pressure to give 41.96 g of an oil. The oil was crystallized from 220 ml of toluene-hexane (1:1) to give 24.94 g of crystals, mp 162°-164° C.

Workup

customThe mixture was evaporated under reduced pressure

Sources & evidence

ORD record: ord-2f960f81459b4c468e71e3018fed7dee
Source dataset: uspto-grants-1992_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05104869

Reaction notes

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