Hydrochloric Acid → 2-(4-Chloro-trans-2-butenyloxy)-benzaldehyde

HRID 1702216Notes

Reaction equation

HRID 1702216 reaction equation
C[O-].[Na+].[CH:4](=[O:12])[C:5]1[C:6](=[CH:8][CH:9]=[CH:10][CH:11]=1)[OH:7].[Cl:13][CH2:14]/[CH:15]=[CH:16]/[CH2:17]Cl.Cl>O.C1(C)C=CC=CC=1.C(O)C>[Cl:13][CH2:14]/[CH:15]=[CH:16]/[CH2:17][O:7][C:6]1[CH:8]=[CH:9][CH:10]=[CH:11][C:5]=1[CH:4]=[O:12]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 6998SalicylaldehydeHCID 6421971,4-Dichloro-2-butene, (2E)-HCID 10942334Sodium Methoxide

Product 1

HCID 155727102-(4-Chloro-trans-2-butenyloxy)-benzaldehyde

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

To 130 lt of ethanol, 12.1 kg of sodium methoxide are added while cooling and stirring, followed by 26.5 kg of salicylaldehyde at 30°. Thereupon 33.3 kg of trans-1,4-dichloro-2-butene are added and the mixture heated to 68° for 4 hours. It is combined with 156 lt of toluene, 187 lt of water and 9.4 kg of 36% hydrochloric acid while keeping the temperature at about 30°. The precipitate formed is filtered off and washed with 16 lt of toluene. The filtrate is separated, the organic layer washed 3 times with 27 lt of water, evaporated, the residue distilled and the fraction boiling at 170°/0.2 mmHg collected, to yield the 2-(4-chloro-trans-2-butenyloxy)benzaldehyde.

Workup

  1. temperaturewhile cooling
  2. temperaturethe mixture heated to 68° for 4 hours
  3. customat about 30°
  4. customThe precipitate formed
  5. filtrationis filtered off
  6. washwashed with 16 lt of toluene
  7. customThe filtrate is separated
  8. washthe organic layer washed 3 times with 27 lt of water
  9. customevaporated
  10. distillationthe residue distilled
  11. customthe fraction boiling at 170°/0.2 mmHg collected

Sources & evidence

ORD record
ord-76f0540fe4bd45e691f5264bf13d99cf
Source dataset
uspto-grants-1983_04
Patent number
US04380653

Reaction notes

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