Hydrochloric Acid → p-(2-Methylbutoxycarbonyl)benzaldehyde

HRID 482817Notes

Reaction equation

HRID 482817 reaction equation
[C:1](Cl)(=[O:10])[C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.[CH2:12]([OH:17])[CH:13]([CH2:15][CH3:16])[CH3:14].N1C=CC=CC=1.Cl>C1(C)C=CC=CC=1>[CH3:14][CH:13]([CH2:15][CH3:16])[CH2:12][O:17][C:1]([C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1)=[O:10]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 87232-Methyl-1-butanolHCID 124246204-Formylbenzoyl chloride

Product 1

HCID 13548338p-(2-Methylbutoxycarbonyl)benzaldehyde

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

315 g of said terephthalaldehydic acid chloride dissolved in 400 ml of toluene was dropped into an ice-cooled mixed solution of commercially available S(-)-2-methylbutanol (optically active amyl alcohol) and 230 g of pyridine, and heated under reflux for 2 hours. The reaction solution was cooled to room temperature and further cooled with ice, and acidified by adding 6N hydrochloric acid thereto to remove pyridine in the organic layer. The organic layer was then washed successively with water, 2N aqueous sodium hydroxide solution, and again with water. Toluene as a solvent was distilled off in vacuum, and the remaining reaction product was distilled in vacuum to obtain p-(2-methylbutoxycarbonyl)benzaldehyde (b.p. 118°-124° C./3.5 Torr).

Workup

  1. temperaturecooled
  2. temperatureheated
  3. temperatureunder reflux for 2 hours
  4. temperaturefurther cooled with ice
  5. customto remove pyridine in the organic layer
  6. washThe organic layer was then washed successively with water, 2N aqueous sodium hydroxide solution
  7. distillationToluene as a solvent was distilled off in vacuum
  8. customthe remaining reaction product
  9. distillationwas distilled in vacuum

Sources & evidence

ORD record
ord-5c338641cfe64aec9b618a3af3a4c4c7
Source dataset
uspto-grants-1986_03
Patent number
US04576732

Reaction notes

Loading…