Benzaldehyde → Acetaldehyde

HRID 652833Notes

Reaction equation

HRID 652833 reaction equation
[OH-].[Na+].[CH:3](=[O:12])[CH:4]=[CH:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[CH:13](=[O:20])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.O.[CH:22](=[O:29])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>O>[CH:13](=[O:20])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[CH:3](=[O:12])[CH:4]=[CH:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[CH3:3][O:12][C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=1[CH:22]=[O:29].[CH:3](=[O:12])[CH3:4]

Participants

9

Reactant 4

HCID 240BenzaldehydeHCID 3073-Phenylprop-2-EnalHCID 14798Sodium Hydroxide2×HCID 86741597HCID 86741597, compound2×

Product 4

HCID 177AcetaldehydeHCID 240BenzaldehydeHCID 3073-Phenylprop-2-EnalHCID 86582-Methoxybenzaldehyde

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
105 °C

Procedure

The above prepared sodium hydroxide solution was then added to the cassia oil and introduced into the pot of the still. The pot was equipped with a stirrer. Using pressurized steam and vigorous stirring, the pot was heated to reflux with a pot temperature of 105° C. Reflux was established with a column head temperature of about 99° C. Once reflux was established, it was continued for about 1 hour. During the course of the conversion of the cinnamaldehyde in the cassia oil to benzaldehyde, pH was monitored and was maintained at about 12 to about 12.5. In the event the pH fell below about 12, sodium hydroxide was added to bring the pH back up to the range of about 12-12.5. After refluxing for about 1 hour, take-off of the water-benzaldehyde azeotrope was initiated. The water cooled condenser was operated at 100° F. thereby enabling the water-benzaldehyde azeotrope to be condensed and collected in a chilled receiver. The acetaldehyde by-product was principally vaporized at the temperature of the condenser and was taken off as vapor. The distillate principally containing benzaldehyde in an amount of about 75% or more with minor amounts of cinnamaldehyde, terpenes, orthomethoxybenzaldehyde and acetaldehyde was obtained. The crude benzaldehyde was thus collected in a chilled receiver and, in a continuous feed operation the condensed water was continuously fed back to the still to replace what had been taken off and the distillation of the azeotrope continued. The fractional steam distillation of the crude benzaldehyde continued until about 670 lbs. of crude benzaldehyde were obtained. The crude distillate containing benzaldehyde was then dried under vacuum and fractionally distilled under vacuum of about 29" thereby providing a boiling point for the benzaldehyde at about 70° C. in order to obtain a substantially pure benzaldehyde free from residual terpenes and other impurities.

Workup

  1. additionwas then added to the cassia oil
  2. additionintroduced into the pot of the still
  3. customThe pot was equipped with a stirrer
  4. temperaturethe pot was heated
  5. temperatureReflux
  6. customwas established with a column head temperature of about 99° C
  7. temperatureOnce reflux
  8. temperaturewas maintained at about 12 to about 12.5
  9. additionwas added
  10. customwas operated at 100° F.
  11. customcondensed
  12. customcollected in a chilled receiver

Sources & evidence

ORD record
ord-77f9a1e6fcc045ea9b47dab90cc0ba96
Source dataset
uspto-grants-1987_06
Patent number
US04673766

Reaction notes

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