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

HRID 470056Notes

Reaction equation

HRID 470056 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, 1 H), 6.96-6.98 (d, J=8 Hz, 1 H), 6.26-6.27 (d, J=4 Hz, 1 H), 6.17-6.19 (m, 1 H), 3.68-3.69 (m, 2 ), 3.56-3.59 (m, 4 H), 3.39 (s, 3 H), 1.37 (s, 6 H); 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-321066368b3444869f44a967030856e4
Source dataset
uspto-grants-2014_01
Patent number
US08629162B2

Reaction notes

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