5-Fluorobenzene-1,3-diol → Umbelliferone

HRID 253720

Reaction equation

HRID 253720 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-Fluorobenzene-1,3-diol

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-6b3dab5e691549ec9674ed348d6cad28
Source dataset
uspto-grants-2011_01
Patent number
US07872142B2

Linked notes

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