Hydrochloric Acid → 4-[2-(Dimethylamino)ethoxy]phenol

HRID 133772Notes

Reaction equation

HRID 133772 reaction equation
C([O:8][C:9]1[CH:20]=[CH:19][C:12]([O:13][CH2:14][CH2:15][N:16]([CH3:18])[CH3:17])=[CH:11][CH:10]=1)C1C=CC=CC=1.Cl>C(O)C>[CH3:17][N:16]([CH3:18])[CH2:15][CH2:14][O:13][C:12]1[CH:19]=[CH:20][C:9]([OH:8])=[CH:10][CH:11]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 59447665[2-(4-Benzyloxyphenoxy)ethyl]dimethylamine

Product 1

HCID 135762384-[2-(Dimethylamino)ethoxy]phenol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A stirred solution of [2-(4-benzyloxyphenoxy)ethyl]dimethylamine (3.36 g, 0.01238 mol) in the mixture of 6 M HCl (67 ml) and ethanol (33.5 ml) was refluxed for 6.5 h. Then ethanol was evaporated and pH was adjusted to 8 with 2.5 M NaOH. The product was extracted into ethyl acetate. The extracts were washed with water and dried over Na2SO4. Removal of solvent under reduced pressure gave a raw product which was purified by flash chromatography on silica gel using heptane/ethyl acetate (9:1-6:4) as a gradient eluent. 1H NMR (300 MHz, DMSO-d6): 2.20 (6H, s), 2.57 (2H, t, 3J=5.9 Hz), 3.92 (2H, t, 3J=5.9 Hz), 6.65 (2H, d, 3J=9.1 Hz), 6.74 (2H, d, 3J=9.0 Hz), 8.85 (1H, s, —OH).

Workup

  1. temperaturewas refluxed for 6.5 h
  2. customThen ethanol was evaporated
  3. extractionThe product was extracted into ethyl acetate
  4. washThe extracts were washed with water
  5. dry with materialdried over Na2SO4
  6. customRemoval of solvent under reduced pressure

Sources & evidence

ORD record
ord-20d584791a364af6bb5b4b90b1b9dbdd
Source dataset
uspto-grants-2008_06
Patent number
US07390923B2

Reaction notes

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