Hydrochloric Acid → 2-(1-(2-Methoxyethoxy)-2-methylpropan-2-yl)-5-aminophenol

HRID 401350Notes

Reaction equation

HRID 401350 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([NH:17]C(=O)C)[CH:5]=[CH:6][C:7]=1[C:8]([CH3:16])([CH3:15])[CH2:9][O:10][CH2:11][CH2:12][O:13][CH3:14].Cl.C([O-])([O-])=O.[Na+].[Na+]>>[CH3:14][O:13][CH2:12][CH2:11][O:10][CH2:9][C:8]([C:7]1[CH:6]=[CH:5][C:4]([NH2:17])=[CH:3][C:2]=1[OH:1])([CH3:16])[CH3:15]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 57567341HCID 57567341, compound

Product 1

HCID 574702502-(1-(2-Methoxyethoxy)-2-methylpropan-2-yl)-5-aminophenolYield 7.3%

Procedure

A mixture of N-{3-hydroxy-4-[2-(2-methoxy-ethoxy)-1,1-dimethyl-ethyl]-phenyl}-acetamide (1 g, 3.5 mmol) and HCl (5 mL) was heated at reflux for 1 h. The mixture was basified with Na2CO3 solution to pH 9 and then extracted with EtOAc (20 mL×3). The combined organic layers were washed with water and brine, dried over Na2SO4 and concentrated to dryness. The residue was purified by column chromatography (petroleum ether-EtOAc, 100:1) to obtain 2-(1-(2-methoxyethoxy)-2-methylpropan-2-yl)-5-aminophenol (C-25) (61 mg, 6%). 1HNMR (CDCl3) δ 9.11 (br s, 1H), 6.96-6.98 (d, J=8 Hz, 1H), 6.26-6.27 (d, J=4 Hz, 1H), 6.17-6.19 (m, 1H), 3.68-3.69 (m, 2H), 3.56-3.59 (m, 4H), 3.39 (s, 3H), 1.37 (s, 6H); ESI-MS 239.9 m/z (MH+).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 1 h
  3. extractionextracted with EtOAc (20 mL×3)
  4. washThe combined organic layers were washed with water and brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated to dryness
  7. customThe residue was purified by column chromatography (petroleum ether-EtOAc, 100:1)

Sources & evidence

ORD record
ord-db1d3908cb994759aa681592be2621c9
Source dataset
uspto-grants-2014_06
Patent number
US08741925B2

Reaction notes

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