Benzaldehyde → 3-Phenylmethylene-5-butyldihydro-2(3H)-furanone

HRID 1111317Notes

Reaction equation

HRID 1111317 reaction equation
[C:1]([CH:4]1[CH2:8][CH:7]([CH2:9][CH2:10][CH2:11][CH3:12])[O:6][C:5]1=[O:13])(=O)[CH3:2].[OH-].[Na+].C(=O)[C:17]1[CH:22]=[CH:21]C=[CH:19][CH:18]=1>>[C:2]1([CH:1]=[C:4]2[CH2:8][CH:7]([CH2:9][CH2:10][CH2:11][CH3:12])[O:6][C:5]2=[O:13])[CH:21]=[CH:22][CH:17]=[CH:18][CH:19]=1

Participants

4

Reactant 3

HCID 240BenzaldehydeHCID 14798Sodium HydroxideHCID 108561723-Acetyl-5-butyloxolan-2-one

Product 1

HCID 545082643-Phenylmethylene-5-butyldihydro-2(3H)-furanone

Procedure

3-Phenylmethylene-5-butyldihydro-2(3H)-furanone was prepared by reacting 3-acetyl-5-butyldihydro-2(3H)-furanone with sodium hydroxide and benzaldehyde in accordance with the procedure described in Example I. The crude product (64.5% yield) was recovered by distillation of the reaction mixture at 25°-147° C. (0.04 mm/Hg) to remove light ends. The structure was confirmed by proton nuclear magnetic resonance spectroscopy. 1HNMR (CDCl3) δ7.5 (m,6H), 4.56 (pentet,1H),3.3 (ddd,1H) 2.8 (ddd,1H) 1.9-1.2 (m,6H), 0.86(t,3H)

Sources & evidence

ORD record
ord-0b975781b62347abae401b820f02e975
Source dataset
uspto-grants-1990_12
Patent number
US04980342

Reaction notes

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