4-Chlorobenzaldehyde → HCID 54478576, compound

HRID 359141Notes

Reaction equation

HRID 359141 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[CH:4][CH:3]=1.[CH3:10][C:11]([CH3:18])([C:15](=[O:17])[CH3:16])[CH2:12][CH:13]=[CH2:14].[OH-].[Na+]>C(O)C.O.[OH-].[Na+]>[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[CH:16][C:15](=[O:17])[C:11]([CH3:18])([CH3:10])[CH2:12][CH:13]=[CH2:14])=[CH:4][CH:3]=1

Participants

7

Reactant 3

HCID 77264-ChlorobenzaldehydeHCID 14798Sodium HydroxideHCID 126041733,3-Dimethylhex-5-en-2-one

Product 1

HCID 54478576HCID 54478576, compoundYield 92.5%

Reagents, catalysts & solvents 3

HCID 14798Sodium HydroxideCatalystHCID 702EthanolSolventHCID 962WaterSolvent3×

Procedure

40 ml of water are added to a solution of 56.2 g (0.4 mol) of 4-chlorobenzaldehyde and 50.4 g (0.4 mol) of 4,4-dimethyl-1-hexen-5-one in 200 ml of ethanol and directly thereafter a solution of 1.2 g of sodium hydroxide in 12 ml of water is added. The mixture is initially stirred for 1 hour at room temperature, then 0.8 g of solid sodium hydroxide is added and the mixture is stirred for a further 16 hours. It is then diluted with water and extracted with ethyl acetate. The ethyl acetate extract is washed three times with water, dried and concentrated. 92 g (92.5% of theory) of 1-(4-chlorophenyl)-4,4-dimethyl-1,6-heptadien-3-one are obtained in the form of a yellow oil. ##STR32##

Workup

  1. stirringthe mixture is stirred for a further 16 hours
  2. extractionextracted with ethyl acetate
  3. extractionThe ethyl acetate extract
  4. washis washed three times with water
  5. customdried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-31c62062847946868335b43272fa8c42
Source dataset
uspto-grants-1991_03
Patent number
US04999440

Reaction notes

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