Hydrochloric Acid → HCID 19068310, compound

HRID 1957589Notes

Reaction equation

HRID 1957589 reaction equation
[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][NH2:13].[CH3:14][O:15][C:16]1[CH:21]=[CH:20][C:19]([CH:22]=O)=[CH:18][C:17]=1[OH:24].C(OC(C)C)(C)C.Cl.[OH-].[Na+]>C(OCC)(=O)C.C(O)(=O)C>[CH2:12]([NH:13][CH2:22][C:19]1[CH:20]=[CH:21][C:16]([O:15][CH3:14])=[C:17]([OH:24])[CH:18]=1)[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 7914Diisopropyl EtherHCID 12127IsovanillinHCID 13583DodecylamineHCID 14798Sodium Hydroxide

Product 1

HCID 19068310HCID 19068310, compoundYield 80.9%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 8857Ethyl AcetateSolvent

Procedure

In a 100-ml round-bottomed flask were placed n-laurylamine (11.1 g (60 mmol)) and isovaniline (1.52 g (10 mmol)) under nitrogen. While stirring, diisopropylether (17.5 ml) and glacial acetic acid (5 ml) were sequentially added dropwise. After completion of addition, the mixture was stirred for approximately 2 hours at room temperature, followed by the addition of a borane-pyridine complex (1.2 ml (10 mmol), product of Aldrich) over 10 minutes. The mixture was stirred for a further 2 hours. Subsequently, 5N-HCl (12 ml) was added dropwise and the resultant mixture was stirred for 10 minutes. The pH of the mixture was turned to basic using an aqueous 5N--NaOH solution. The product formed was extracted using diisopropyl ether, concentrated, and purified via silica gel column chromatography n-hexane:ethyl acetate=2:1), thereby obtaining 2.6 g of N-lauryl-3-hydroxy-4-methoxybenzylamine as mud yellow crystals (yield: 82%).

Workup

  1. customIn a 100-ml round-bottomed flask were placed
  2. additionAfter completion of addition
  3. stirringthe mixture was stirred for approximately 2 hours at room temperature
  4. additionfollowed by the addition of a borane-pyridine complex (1.2 ml (10 mmol), product of Aldrich) over 10 minutes
  5. stirringThe mixture was stirred for a further 2 hours
  6. customThe product formed
  7. extractionwas extracted
  8. concentrationconcentrated
  9. custompurified via silica gel column chromatography n-hexane

Sources & evidence

ORD record
ord-1069f21e60ee4af093c918e43936e1f8
Source dataset
uspto-grants-1998_07
Patent number
US05786386

Reaction notes

Loading…