Sodium Carbonate → 6-Hydroxy-chroman-4-one

HRID 2306279Notes

Reaction equation

HRID 2306279 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[O:9][CH2:8][CH2:7][C:6]2=[O:13].C([O-])([O-])=O.[Na+].[Na+]>Br.CC(O)=O>[OH:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[O:9][CH2:8][CH2:7][C:6]2=[O:13]

Participants

5

Reactant 2

HCID 10340Sodium CarbonateHCID 46121686-methoxy-3,4-dihydro-2H-1-benzopyran-4-one

Product 1

HCID 70989446-Hydroxy-chroman-4-one

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 260Hydrogen BromideSolvent

Procedure

A solution of 6-methoxy-2,3-dihydro-4H-chromen-4-one in 48% aqueous HBr (250 mL) and HOAc (250 mL) was heated to 75° C. for 6 hours. The reaction mixture was cooled, adjusted to pH≈5 by the addition of saturated aqueous Na2CO3 and extracted with CHCl3 (2×75 mL). The combined organic extracts were dried over MgSO4, filtered, and concentrated in vacuo to give the desired compound.

Workup

  1. temperatureThe reaction mixture was cooled
  2. extractionextracted with CHCl3 (2×75 mL)
  3. dry with materialThe combined organic extracts were dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-39cdfb81a635443ba685088b485d0806
Source dataset
uspto-grants-2002_08
Patent number
US06441017B1

Reaction notes

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