Acetic Acid → 2-n-Pentyl-3-(2,4-dichlorophenyl)-acrolein

HRID 2418265Notes

Reaction equation

HRID 2418265 reaction equation
[CH:1](=[O:8])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7].[Cl:9][C:10]1[CH:17]=[C:16]([Cl:18])[CH:15]=[CH:14][C:11]=1[CH:12]=O.[OH-].[Na+].C(O)(=O)C>CO>[CH2:3]([C:2](=[CH:12][C:11]1[CH:14]=[CH:15][C:16]([Cl:18])=[CH:17][C:10]=1[Cl:9])[CH:1]=[O:8])[CH2:4][CH2:5][CH2:6][CH3:7]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 8130HeptanalHCID 134042,4-DichlorobenzaldehydeHCID 14798Sodium Hydroxide

Product 1

HCID 538223112-n-Pentyl-3-(2,4-dichlorophenyl)-acroleinYield 61.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

342 g of heptanal were added dropwise to a solution of 525 g of 2,4-dichlorobenzaldehyde and 12 g of NaOH in 1.5 l of methanol in the course of 6 hours. The mixture was allowed to continue reacting for 1 hour, then acidified with glacial acetic acid, and concentrated after a further 15 hours. The residue was taken up in CH2Cl2 /H2O, and the organic phase was washed with water, dried over Na2SO4 and concentrated. Distillation of the residue gave 498 g of (I) of boiling point 152°-160° C./0.2 mbar.

Workup

  1. concentrationconcentrated after a further 15 hours
  2. washthe organic phase was washed with water
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. distillationDistillation of the residue

Sources & evidence

ORD record
ord-c1cff1e4cb5047989d7b0d11a7379927
Source dataset
uspto-grants-1984_09
Patent number
US04472412

Reaction notes

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