5-Fluororesorcinol → Umbelliferone

HRID 1795445Notes

Reaction equation

HRID 1795445 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-b37451d75d234d86ab5520d8c78ba42f
Source dataset
uspto-grants-2006_04
Patent number
US07026491B2

Reaction notes

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