Hydrochloric Acid → 2-Isopropyl-4,5-dimethoxy-benzaldehyde

HRID 81744Notes

Reaction equation

HRID 81744 reaction equation
[CH:1]([C:4]1[CH:18]=[C:17]([O:19][CH3:20])[C:16]([O:21][CH3:22])=[CH:15][C:5]=1[CH:6]=NC(C(C)C)C(C)C)([CH3:3])[CH3:2].Cl.C1C[O:27]CC1>>[CH:1]([C:4]1[CH:18]=[C:17]([O:19][CH3:20])[C:16]([O:21][CH3:22])=[CH:15][C:5]=1[CH:6]=[O:27])([CH3:3])[CH3:2]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 59598696(2-Isopropyl4,5-dimethoxy-benzylidene)-(1-isopropyl-2-methyl-propyl)-amine

Product 1

HCID 541451142-Isopropyl-4,5-dimethoxy-benzaldehydeYield 43%

Procedure

(2-Isopropyl-4,5-dimethoxy-benzylidene)-(1-isopropyl-2-methyl-propyl)-amine was dissolved in 30 ml of THF. HCl (4.1 mL, 4 M) was added and the mixture was warmed to reflux. After 3 hours the mixture was cooled concentrated in vacuo. 100 mL of H2O was added and the mixture was extracted with ethyl acetate, washed with H2O and then with brine. The combined organic layers were dried over Na2SO4, filtered and concentrated in vacuo to give an orange oil. Purification via flash chromatography (85:15 hexane/ethyl acetate) gave 2-isopropyl-4,5-dimethoxy-benzaldehyde (0.331 g, 43%) as a clear oil

Workup

  1. temperaturethe mixture was warmed to reflux
  2. temperatureAfter 3 hours the mixture was cooled
  3. concentrationconcentrated in vacuo
  4. addition100 mL of H2O was added
  5. extractionthe mixture was extracted with ethyl acetate
  6. washwashed with H2O
  7. dry with materialThe combined organic layers were dried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customto give an orange oil
  11. customPurification via flash chromatography (85:15 hexane/ethyl acetate)

Sources & evidence

ORD record
ord-249d6e4d4cc54656b76d25a934cd66b0
Source dataset
uspto-grants-2014_09
Patent number
US08846705B2

Reaction notes

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