Isobutyraldehyde → HCID 53840005, compound

HRID 2050406Notes

Reaction equation

HRID 2050406 reaction equation
[Cl:1][C:2]1[CH:9]=[C:8]([F:10])[CH:7]=[CH:6][C:3]=1[CH2:4]Cl.[CH:11](=[O:15])[CH:12]([CH3:14])[CH3:13].[OH-].[Na+]>C1(C)C=CC=CC=1.[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[Cl:1][C:2]1[CH:9]=[C:8]([F:10])[CH:7]=[CH:6][C:3]=1[CH2:4][C:12]([CH3:14])([CH3:13])[CH:11]=[O:15]

Participants

6

Reactant 3

HCID 6561IsobutyraldehydeHCID 14798Sodium HydroxideHCID 27250642-Chloro-1-(chloromethyl)-4-fluorobenzene

Product 1

HCID 53840005HCID 53840005, compoundYield 57.9%

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 1140TolueneSolvent2×

Procedure

65.0 g of 2-chloro-4-fluorobenzyl chloride in 90 ml of toluene and 28.8 g of isobutyraldehyde are added dropwise, simultaneously but separately, with thorough mixing at 80° C. in the course of 30 minutes to a mixture of 1.9 g of tetrabutylammonium iodide, 155 g of 30% strength sodium hydroxide solution and 115 ml of toluene, and stirring is continued for 3 hours at 80° C. The organic phase is separated off, washed with three times 50 ml of water, dried, and concentrated (58.5 g) by short-path distillation (bp.=70°-90° C./0.3). Distillation gives 45.1 g of (2-chloro-4-fluorophenyl)-pivalaldehyde (bp.: 53°-55° C./0.1).

Workup

  1. customThe organic phase is separated off
  2. washwashed with three times 50 ml of water
  3. customdried
  4. concentrationconcentrated (58.5 g)
  5. distillationby short-path distillation (bp.=70°-90° C./0.3)
  6. distillationDistillation

Sources & evidence

ORD record
ord-2addd1b5522a467699a2191e4079b320
Source dataset
uspto-grants-1991_05
Patent number
US05013354

Reaction notes

Loading…