Hydrochloric Acid → HCID 86599471, compound

HRID 854930Notes

Reaction equation

HRID 854930 reaction equation
[C:1]1([C:7]([C:9]2[CH:10]=[C:11]([OH:15])[CH:12]=[CH:13][CH:14]=2)=[CH2:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Mg+2].[Cl-].[Cl-].[CH2:19]=[O:20].Cl>C(#N)C>[OH:15][C:11]1[CH:10]=[C:9]([C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)=[CH2:8])[CH:14]=[CH:13][C:12]=1[CH:19]=[O:20]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 712Formaldehyde2×HCID 5360315Magnesium Chloride2×HCID 15645631HCID 15645631, compound

Product 1

HCID 86599471HCID 86599471, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of the phenol from step 2 (4.15 g, 21.1 mmole), MgCl2 (3.02 g, 31.7 mmole), TEA (11.1 mL, 79.3 mmole) and paraformaldehyde (4.29 g, 143 mmole) in anhydrous acetonitrile (100 mL) was refluxed for 17 h. Additional MgCl2 (1.5 g, 15.8 mmole), TEA (5.6 mL, 40 mmole) and paraformaldehyde (2.23 g, 74 mmole) were then added and reflux was continued for 2 h. The mixture was then cooled, acidified with 1N HCl and extracted with EtOAc (2×200 mL). The combined extracts were washed with brine (100 mL), dried over MgSO4, filtered and concentrated in vacuo. The crude product was purified by filtration through a silica-gel plug (9:1 hexanes:EtOAc) to give 4.28 g (91% yield) of the product as a yellow oil: EIHRMS m/z 224.0837 (M+, C15H12O2, Calc'd 224.0837).

Workup

  1. temperaturewas refluxed for 17 h
  2. temperaturereflux
  3. temperatureThe mixture was then cooled
  4. extractionextracted with EtOAc (2×200 mL)
  5. washThe combined extracts were washed with brine (100 mL)
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. filtrationThe crude product was purified by filtration through a silica-gel plug (9:1 hexanes:EtOAc)

Sources & evidence

ORD record
ord-050b6fb6b98f4ff28ef6c64d34a5e134
Source dataset
uspto-grants-2007_08
Patent number
US07259266B2

Reaction notes

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