Sodium Chloride → HCID 54024121, compound
Reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[Cl:10])[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]=[CH:8][C:9]=1[Cl:10]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 60 °C
Procedure
To a solution of 3,4-dichlorobenzaldehyde (2.3 g, 13.2 mM) and 2,2,5-trimethyl-3(2H)-furanone (2.0 g, 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 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 (2.1 g, 56% yield), m.p. 100°-102° C.
Workup
- temperatureAfter the reaction solution 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-1e864c7300d9410e80ac481cf599baf1
- Source dataset
- uspto-grants-1991_03
- Patent number
- US05001126
Reaction notes
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