Water → HCID 68745479, compound

HRID 2242785Notes

Reaction equation

HRID 2242785 reaction equation
[C:1]([CH:4]1[CH2:9][CH2:8][O:7][C:5]1=[O:6])(=O)[CH3:2].[OH-].[Na+].O.[CH:13]1(C=O)[CH2:18][CH2:17]C[CH2:15][CH2:14]1>C1(C)C=CC=CC=1>[CH:2]1([CH:1]=[C:4]2[CH2:9][CH2:8][O:7][C:5]2=[O:6])[CH2:17][CH2:18][CH2:13][CH2:14][CH2:15]1

Participants

6

Reactant 4

HCID 962WaterHCID 106012-AcetylbutyrolactoneHCID 14798Sodium HydroxideHCID 16275Cyclohexanecarboxaldehyde

Product 1

HCID 68745479HCID 68745479, compoundYield 21%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 2-acetyl-γ-butyrolactone (15.4 g) in toluene (100 mL) was treated portionwise with sodium hydroxide (4.8 g) during 10 min and then refluxed with a Dean & Stark moisture receiver until the formation of water had stopped (about 1 h). After that the reaction mixture was treated dropwise with cyclohexanecarbaldehyde (15.0 g) during 1 h. Upon completion of the addition, the mixture was refluxed for 4 h, then cooled to room temperature and washed with water. After drying over magnesium sulfate, the obtained organic phase was filtered, concentrated on a rotary evaporator and distilled in vacuum to give 4.54 g (21%) of the title compound.

Workup

  1. custom(about 1 h)
  2. additionUpon completion of the addition
  3. temperaturethe mixture was refluxed for 4 h
  4. washwashed with water
  5. dry with materialAfter drying over magnesium sulfate
  6. filtrationthe obtained organic phase was filtered
  7. concentrationconcentrated on a rotary evaporator
  8. distillationdistilled in vacuum

Sources & evidence

ORD record
ord-f3d6bcdc7d1a4f0db3e5294cbe373ff1
Source dataset
uspto-grants-2010_03
Patent number
US07674741B2

Reaction notes

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