Phloroglucinol → 2-Methoxy-1-(2,4,6-trihydroxyphenyl)ethanone

HRID 1506834

Reaction equation

HRID 1506834 reaction equation
[C:1]1([CH:9]=[C:7]([OH:8])[CH:6]=[C:4]([OH:5])[CH:3]=1)[OH:2].[CH3:10][O:11][CH2:12][C:13]#N.C([O:17]CC)C>[Cl-].[Zn+2].[Cl-]>[CH3:10][O:11][CH2:12][C:13]([C:9]1[C:1]([OH:2])=[CH:3][C:4]([OH:5])=[CH:6][C:7]=1[OH:8])=[O:17]

Participants

5

Reactant 3

HCID 359PhloroglucinolHCID 3283Diethyl EtherHCID 74442Methoxyacetonitrile

Product 1

HCID 6434002-Methoxy-1-(2,4,6-trihydroxyphenyl)ethanoneYield 81%

Reagents, catalysts & solvents 1

HCID 3007855ZincchlorideCatalyst

Procedure

Phloroglucinol (35.1 g, 279 mmol) was dissolved into ethyl ether (500 mL) solution, followed by zinc chloride (8 g, 59 mmol) and 2-methoxy acetonitrile (18 g, 253 mmol) added in the solution under ice water bath condition. Dry HCl gas was bubbled into the reaction mixture, vigorously stirring for 5 hours, and precipitate was formed. The precipitate was filtered and collected, followed by dissolved into water and refluxed for 3 hours. After cooling, pink precipitate was collected, and desired white compound can be obtained after recrystallization with water. (45 g, yield 81%) 1HNMR (400 MHz, DMSO-d6): δ=12.14 (s, 2H), 10.41 (s, 1H), 5.79 (s, 2H), 4.56 (s, 2H), 3.32 (s, 3H).

Workup

  1. additionadded in the solution under ice water bath condition
  2. customDry HCl gas was bubbled into the reaction mixture
  3. customprecipitate was formed
  4. filtrationThe precipitate was filtered
  5. customcollected
  6. dissolutionby dissolved into water
  7. temperaturerefluxed for 3 hours
  8. temperatureAfter cooling
  9. custompink precipitate was collected
  10. customdesired white compound can be obtained
  11. customafter recrystallization with water

Sources & evidence

ORD record
ord-3fe139a606c14a0d83c37aa1a17f3b1e
Source dataset
uspto-grants-2015_12
Patent number
US09221781B2

Linked notes

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