Tert-Butylamine → 4-[3-(tert-Butylamino)-2-hydroxypropoxy]benzaldehyde

HRID 325345Notes

Reaction equation

HRID 325345 reaction equation
[O:1]1[CH2:13][CH:2]1[CH2:3][O:4][C:5]1[CH:12]=[CH:11][C:8]([CH:9]=[O:10])=[CH:7][CH:6]=1.[C:14]([NH2:18])([CH3:17])([CH3:16])[CH3:15]>Cl>[C:14]([NH:18][CH2:13][CH:2]([OH:1])[CH2:3][O:4][C:5]1[CH:12]=[CH:11][C:8]([CH:9]=[O:10])=[CH:7][CH:6]=1)([CH3:17])([CH3:16])[CH3:15]

Participants

4

Reactant 2

HCID 6385Tert-ButylamineHCID 2736334HCID 2736334, compound

Product 1

HCID 125215864-[3-(tert-Butylamino)-2-hydroxypropoxy]benzaldehyde

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

To 4-(2,3-epoxypropoxy)benzaldehyde (20 g.) is added tert. butylamine (50 ml.) and the resulting solution is refluxed 17 hours. The excess tert. butylamine is removed by heating at atmospheric pressure to yield a solid residue. To this residue is added 6 N hydrochloric acid (200 ml.) and the resulting mixture is heated 5 hours on a steam bath. The solution is cooled and concentrated to 100 ml. on a steam bath under reduced pressure (20 mm. Hg.). The concentrated solution is made basic to pH 10 with saturated aqueous sodium carbonate and extracted with chloroform. The chloroform extract is concentrated to a solid which after recrystallization from acetonitrile yields 18 g. of 4-(3-tert.butylamino-2-hydroxypropxy)benzaldehyde, m.p. 123°-125.5° C.

Workup

  1. temperaturethe resulting solution is refluxed 17 hours
  2. customThe excess tert. butylamine is removed
  3. temperatureby heating at atmospheric pressure
  4. customto yield a solid residue
  5. temperaturethe resulting mixture is heated 5 hours on a steam bath
  6. temperatureThe solution is cooled
  7. concentrationconcentrated to 100 ml
  8. extractionextracted with chloroform
  9. extractionThe chloroform extract
  10. concentrationis concentrated to a solid which
  11. customafter recrystallization from acetonitrile
  12. customyields 18 g

Sources & evidence

ORD record
ord-d13b5ee46724466eb636c8122a68cb2a
Source dataset
uspto-grants-1984_04
Patent number
US04440774

Reaction notes

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