Sodium Chloride → HCID 54102322, compound

HRID 359363Notes

Reaction equation

HRID 359363 reaction equation
[Cl:1][C:2]1[CH:9]=[C:8]([Cl:10])[CH:7]=[CH:6][C:3]=1[CH:4]=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:9]=[C:8]([Cl:10])[CH:7]=[CH:6][C:3]=1[CH:4]=[CH:18][C:14]1[O:13][C:12]([CH3:19])([CH3:11])[C:16](=[O:17])[CH:15]=1

Participants

6

Reactant 4

HCID 5234Sodium ChlorideHCID 134042,4-DichlorobenzaldehydeHCID 14798Sodium HydroxideHCID 1370803(2H)-Furanone, 2,2,5-trimethyl-

Product 1

HCID 54102322HCID 54102322, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 2,4-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 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 triturated with 10% diethyl ether/pet. ether to afford a light yellow powder (2.6 g, 70% yield), m.p. 154°-156° C.

Workup

  1. temperatureAfter the reaction solution was cooled
  2. extractionThe aqueous layer was extracted with diethyl ether (3×100 mL)
  3. washThe combined ethereal extracts were washed with saturated aqueous sodium chloride (50 mL)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give a yellow solid
  8. customThe crude product was triturated with 10% diethyl ether/pet. ether

Sources & evidence

ORD record
ord-1fb886c3d3f84dff8682a5f7bf147c03
Source dataset
uspto-grants-1991_03
Patent number
US05001126

Reaction notes

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