Sulfuric Acid → HCID 20037278, compound

HRID 1904540Notes

Reaction equation

HRID 1904540 reaction equation
[C:1]1([CH:8]=[CH:7][CH:6]=[C:4]([OH:5])[CH:3]=1)[OH:2].S(=O)(=O)(O)O.[CH3:14][C:15]([CH3:21])=[CH:16][C:17](OC)=[O:18]>>[CH3:14][C:15]1([CH3:21])[C:8]2[C:1](=[CH:3][C:4]([OH:5])=[CH:6][CH:7]=2)[O:2][C:17](=[O:18])[CH2:16]1

Participants

4

Reactant 3

HCID 1118Sulfuric AcidHCID 5054ResorcinolHCID 13546Methyl 3-methyl-2-butenoate

Product 1

HCID 20037278HCID 20037278, compoundYield 27%

Conditions

Temperature
130 °C

Procedure

A mixture of 103 g of resorcinol and 4.6 g of conc. sulfuric acid was heated at 130° C. with stirring, and 58 g of methyl 3,3-dimethylacrylate was added. The mixture was heated at 130° C. for 3 hours with stirring. The reaction mixture was worked up in a customary manner, and the residue after concentration was purified by column chromatography to give 24 g (yield 27%) of 4,4-dimethyl-7-hydroxycoumarin (melting point 84°-85° C.). The product was worked up in the same way as in Referential Example 16 to give 16.8 g (yield 75%) of the desired product as colorless crystals (melting point 88°-88.5° C.).

Workup

  1. temperatureThe mixture was heated at 130° C. for 3 hours
  2. stirringwith stirring
  3. concentrationthe residue after concentration
  4. customwas purified by column chromatography

Sources & evidence

ORD record
ord-55ec40a7db9a4179a42e3a220c48bd15
Source dataset
uspto-grants-1989_06
Patent number
US04838924

Reaction notes

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