5-Fluororesorcinol → Umbelliferone

HRID 2234239Notes

Reaction equation

HRID 2234239 reaction equation
F[C:2]1[CH:7]=[C:6]([OH:8])[CH:5]=[C:4]([OH:9])[CH:3]=1>S(=O)(=O)(O)O>[OH:9][C:4]1[CH:5]=[C:6]2[C:7]([CH:4]=[CH:5][C:6](=[O:8])[O:8]2)=[CH:2][CH:3]=1

Participants

3

Reactant 1

HCID 126587785-Fluororesorcinol

Product 1

HCID 5281426UmbelliferoneYield 146.9%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

1-Fluoro-3,5-dihydroxybenzene (1.0 g, 7.8 mmol) and ethyl 2-benzyl acetoacetate 1.72 g, 7.8 mmol) are suspended in 20 mL of 70% sulfuric acid at room temperature. The reaction mixture is stirred for 24 hours and poured into ice water. The solid is filtered and washed with water. The yellowish crude product is re-crystallized from hot ethanol to afford the 7-hydroxy coumarin intermediate (929 mg, 42%).

Workup

  1. filtrationThe solid is filtered
  2. washwashed with water
  3. customThe yellowish crude product is re-crystallized from hot ethanol

Sources & evidence

ORD record
ord-04fb55f6fdfd43f6a617feee92548d26
Source dataset
uspto-grants-2010_05
Patent number
US07709664B2

Reaction notes

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