Sodium Chloride → 5-[4-(4-Chlorophenyl)-1,3-butadienyl]-2,2-dimethyl-3(2H)-furanone

HRID 359362Notes

Reaction equation

HRID 359362 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][C:5]([CH:6]=[CH:7][CH:8]=O)=[CH:4][CH:3]=1.[CH3:12][C:13]1([CH3:20])[C:17](=[O:18])[CH:16]=[C:15]([CH3:19])[O:14]1.[OH-].[Na+].[Cl-].[Na+]>C(O)C>[Cl:1][C:2]1[CH:11]=[CH:10][C:5]([CH:6]=[CH:7][CH:8]=[CH:19][C:15]2[O:14][C:13]([CH3:20])([CH3:12])[C:17](=[O:18])[CH:16]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 5234Sodium ChlorideHCID 14798Sodium HydroxideHCID 1370803(2H)-Furanone, 2,2,5-trimethyl-HCID 3794977p-Chlorocinnamaldehyde

Product 1

HCID 542263425-[4-(4-Chlorophenyl)-1,3-butadienyl]-2,2-dimethyl-3(2H)-furanoneYield 42.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of p-chlorocinnamaldehyde (2.7 g, 16.2 mM) and 2,2,5-trimethyl-3(2H)-furanone (2.45 g, 19.4 mM) in ethanol (100 mL), was added 1N aqueous sodium hydroxide (32 mL, 3.2 mM). The reaction solution was stirred at room temperature for one day. After 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 brown solid. The crude product was purified by chromatography (silica gel, pet. ether-ethyl acetate) to afford yellow crystals (1.9 g, 36% yield), m.p. 95°-96° C.

Workup

  1. extractionthe aqueous layer was extracted with diethyl ether (3×100 mL)
  2. washThe combined ethereal extracts were washed with saturated aqueous sodium chloride (50 mL)
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give a brown solid
  7. customThe crude product was purified by chromatography (silica gel, pet. ether-ethyl acetate)

Sources & evidence

ORD record
ord-775556e7942c468a8e4813c7d972b8c0
Source dataset
uspto-grants-1991_03
Patent number
US05001126

Reaction notes

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