Furfuryl Alcohol → HCID 54101908, compound
Reaction equation
[CH:1]([CH:3]1[CH2:5][C:4]1([C:10]([O:12][CH3:13])=[O:11])[C:6]([O:8][CH3:9])=[O:7])=[CH2:2].C(O)[C:15]1[O:19][CH:18]=[CH:17][CH:16]=1>>[CH:1]([CH:3]1[CH2:5][C:4]1([C:10]([O:12][CH2:13][C:18]1[O:19][CH:15]=[CH:16][CH:17]=1)=[O:11])[C:6]([O:8][CH3:9])=[O:7])=[CH2:2]Participants
Procedure
A transalcoholysis reaction was carried out in a manner similar to that described for Example II using dimethyl 2-vinylcyclopropane-1,1-dicarboxylate (92 g; 0.5 mol) and furfuryl alcohol (24.5 g; 0.25 mol). When essentially all of the furfuryl alcohol was consumed, the reaction mixture was dissolved in ethyl ether and washed with aqueous potassium hydroxide (5%). The ether portion was dried over MgSO4, filtered and vacuum distilled to obtain 21.63 g crude methyl (2-furyl)methyl 2-vinylcyclopropane-1,1-dicarboxylate. B.p. 91°-97° C. at 0.015 mm Hg. The distilled product (M.p. 58°-64° C.) was first recrystallized from methanol and then from a mixture of petroleum ether and methanol to obtain high purity methyl (2-furyl)methyl 2-vinylcyclopropane-1,1-dicarboxylate (translucent crystals melting at 67.5°-68.5° C.). The infrared spectra and nuclear magnetic resonance spectra were consistent with the desired product. Similar results are obtained when (5-methyl-2-furyl)carbinol, (5-allyl-3-furyl)carbinol and 5-hydroxymethyl-2,2'-difuryl methane are substituted for the furfuryl alcohol in the above reaction and all of these products are useful in insecticidal formulations.
Workup
- customA transalcoholysis reaction
- customWhen essentially all of the furfuryl alcohol was consumed
- dissolutionthe reaction mixture was dissolved in ethyl ether
- washwashed with aqueous potassium hydroxide (5%)
- dry with materialThe ether portion was dried over MgSO4
- filtrationfiltered
- distillationvacuum distilled
Sources & evidence
- ORD record
- ord-5d8d3cfb9a6c47558bc6ba601397c135
- Source dataset
- uspto-grants-1983_04
- Patent number
- US04380656
Reaction notes
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