Hydrochloric Acid → HCID 58438669, compound

HRID 217456Notes

Reaction equation

HRID 217456 reaction equation
[F:1][C:2]1[CH:11]=[C:10]([O:12]COC)[CH:9]=[C:8]2[C:3]=1[CH:4]=[C:5]([CH:16]=[O:17])[CH2:6][O:7]2.Cl>CC(C)=O>[F:1][C:2]1[CH:11]=[C:10]([OH:12])[CH:9]=[C:8]2[C:3]=1[CH:4]=[C:5]([CH:16]=[O:17])[CH2:6][O:7]2

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 58438684HCID 58438684, compound

Product 1

HCID 58438669HCID 58438669, compoundYield 77.7%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

5-Fluoro-7-(methoxymethoxy)-2H-chromene-3-carbaldehyde (1.5 g) was dissolved in acetone (25 mL), and 1 M HCl (20 mL) was added thereto, followed by heating and refluxing for 5 hours. The reaction liquid was concentrated and the residue was dissolved in EtOAc, washed with water and brine, and dried over MgSO4, and the filtrate was concentrated. The residue was washed with chloroform to obtain 5-fluoro-7-hydroxy-2H-chromene-3-carbaldehyde (0.95 g) as a yellow powder.

Workup

  1. temperatureby heating
  2. temperaturerefluxing for 5 hours
  3. customThe reaction liquid
  4. concentrationwas concentrated
  5. dissolutionthe residue was dissolved in EtOAc
  6. washwashed with water and brine
  7. dry with materialdried over MgSO4
  8. concentrationthe filtrate was concentrated
  9. washThe residue was washed with chloroform

Sources & evidence

ORD record
ord-81815ff431d749f9bd186cca1c8bef2b
Source dataset
uspto-grants-2012_06
Patent number
US08193378B2

Reaction notes

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