Acetic Acid → 2-[(4-Methoxybenzyl)amino]ethanol

HRID 51300Notes

Reaction equation

HRID 51300 reaction equation
C(O)(=O)C.[CH:5](=O)[C:6]1[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[CH:8][CH:7]=1.[CH2:15]([CH2:17][NH2:18])[OH:16].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>CO>[CH3:13][O:12][C:9]1[CH:10]=[CH:11][C:6]([CH2:5][NH:18][CH2:17][CH2:15][OH:16])=[CH:7][CH:8]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 700EthanolamineHCID 312444-MethoxybenzaldehydeHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 1044692-[(4-Methoxybenzyl)amino]ethanol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Acetic acid (ca. 150 ml) was added to a solution of p-anisaldehyde (58.2 g, 0.42 mol) and ethanolamine (152 ml, 2.52 mol) in methanol (1L), to achieve a pH of 6. Sodium triacetoxyborohydride (100 g, 0.47 mol) was added portionwise, and once addition was complete, the mixture was stirred at room temperature for 72 hours. The mixture was concentrated under reduced pressure, basified using 1N sodium hydroxide solution and extracted with dichloromethane (10×300 ml). The combined extracts were evaporated and the crude product was purified by column chromatography on silica gel using an elution gradient of dichloromethane:methanol (98:2 to 90:10) to afford the title compound, 42 g. 1H-NMR (CDCl3, 400 MHz) δ: 2.78 (t, 2H), 3.62 (t, 2H), 3.75 (m, 5H), 4.24 (s, 2H), 6.81 (d, 2H), 7.22 (d, 2H). LRMS: m/z (ES+) 182 [MH+].

Workup

  1. additiononce addition
  2. concentrationThe mixture was concentrated under reduced pressure
  3. extractionextracted with dichloromethane (10×300 ml)
  4. customThe combined extracts were evaporated
  5. customthe crude product was purified by column chromatography on silica gel using an elution gradient of dichloromethane:methanol (98:2 to 90:10)

Sources & evidence

ORD record
ord-dc5a94fd0a8443ef8975e280b7afffec
Source dataset
uspto-grants-2004_03
Patent number
US06713496B2

Reaction notes

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