Hydrochloric Acid → 1-(2,6-dihydroxyphenyl)-propan-1-one

HRID 843121Notes

Reaction equation

HRID 843121 reaction equation
COC[O:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([O:11]COC)[C:6]=1[C:15](=[O:18])[CH2:16][CH3:17].Cl>CO.O1CCOCC1.C(OCC)(=O)C>[OH:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([OH:11])[C:6]=1[C:15](=[O:18])[CH2:16][CH3:17]

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 22614991HCID 22614991, compound

Product 1

HCID 116223911-(2,6-dihydroxyphenyl)-propan-1-one

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 1-(2,6-bis-methoxymethoxy-phenyl)-propan-1-one (770 mg) in methanol (12 ml) and 1,4-dioxane (12 ml) was added 4N-HCl (2 ml) at room temperature, then the mixture was heated to 50° C. and stirred for 2 hours. The mixture was diluted with ethyl acetate and washed with water (20 ml) and brine (20 ml). The separated organic layer was dried over anhydrous magnesium sulfate and evaporated. The residue was purified by silica gel column chromatography developed by hexane-ethyl acetate. 1-(2,6-dihydroxyphenyl)-propan-1-one was obtained as a yellow solid (398 mg). EI-MS: m/z 178 (M+); 1H-NMR (CDCl3): δ 1.03-1.08 (2H, m), 1.29-1.35 (2H, m), 2.21-2.31 (1H, m), 6.41 (2H, d, J=8.3 Hz), 7.23 (1H, t, J=8.3 Hz) 9.24 (2H, brs).

Workup

  1. washwashed with water (20 ml) and brine (20 ml)
  2. dry with materialThe separated organic layer was dried over anhydrous magnesium sulfate
  3. customevaporated
  4. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-55a783d50a1e4261933027fb0022aeda
Source dataset
uspto-grants-2002_04
Patent number
US06376491B1

Reaction notes

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