Sodium Chloride → HCID 53850744, compound

HRID 359365Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([Cl:10])[CH:9]=1)[CH:5]=O.[CH3:11][C:12]1([CH3:19])[C:16](=[O:17])[CH:15]=[C:14]([CH3:18])[O:13]1.[OH-].[Na+].[Cl-].[Na+]>C(O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:18][C:14]2[O:13][C:12]([CH3:19])([CH3:11])[C:16](=[O:17])[CH:15]=2)[CH:7]=[C:8]([Cl:10])[CH:9]=1

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of 3,5-dichlorobenzaldehyde (2.3 g, 13.2 mM) and 2,2,5-trimethyl-3(2H)-furanone (2.0 gm, 15.9 mM) in ethanol (100 mL), was added 1N aqueous sodium hydroxide (1.6 mL, 1.6 mM). The reaction solution was heated at 60° C. for 4 hours. After the reaction solution was cooled, saturated aqueous sodium chloride (400 mL) was added. The aqueous layer was extracted with diethyl ether (3×100 mL). The combined ethereal extracts were washed with saturated aqueous sodium chloride (50 mL), dried over MgSO4, filtered and concentrated to give a yellow solid. The crude product was purified by chromatography (silica gel, pet. ether/ethyl acetate) to afford a light yellow solid (1.7 g, 45% yield), m.p. 129°-131° C.

Workup

temperatureAfter the reaction solution was cooled
extractionThe aqueous layer was extracted with diethyl ether (3×100 mL)
washThe combined ethereal extracts were washed with saturated aqueous sodium chloride (50 mL)
dry with materialdried over MgSO4
filtrationfiltered
concentrationconcentrated
customto give a yellow solid
customThe crude product was purified by chromatography (silica gel, pet. ether/ethyl acetate)

Sources & evidence

ORD record: ord-25fe2ac6c9ff4bff9d1409d5b2c222db
Source dataset: uspto-grants-1991_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05001126

Reaction notes

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