5-Fluororesorcinol → Umbelliferone

HRID 1671494Notes

Reaction equation

HRID 1671494 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-b699d2efe0e04786b171c1278f5726a9
Source dataset
uspto-grants-2011_08
Patent number
US07994318B2

Reaction notes

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