Resorcinol → HCID 10877698, compound

HRID 1904546Notes

Reaction equation

HRID 1904546 reaction equation
[C:1]1([CH:8]=[CH:7][CH:6]=[C:4]([OH:5])[CH:3]=1)[OH:2].[C:9](O)(=[O:13])/[CH:10]=[CH:11]/[CH3:12]>[Cl-].[Zn+2].[Cl-]>[OH:2][C:1]1[CH:8]=[CH:7][C:6]2[C:9](=[O:13])[CH2:10][CH:11]([CH3:12])[O:5][C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 5054ResorcinolHCID 637090Crotonic Acid

Product 1

HCID 10877698HCID 10877698, compoundYield 41%

Reagents, catalysts & solvents 1

HCID 3007855ZincchlorideCatalyst

Procedure

Resorcinol (11 g) and 17.2 g of crotonic acid were heated at 180° C. for 30 minutes together with 15 g of zinc chloride with stirring. The reaction mixture was extracted with ethyl acetate, and purified by column chromatography to give 7.3 g of 2,3-dihydro-7-hydroxy-2-methyl-4-oxobenzopyran. The OH group of the compound was benzylated in a customary manner, and then the product was reacted with CH3MgBr in tetrahydrofuran. The product was then hydrogenated in ethanol at room temperature for 13 hours in the presence of 5% palladium-carbon. The hydrogenated product was purified by column chromatography to give 4.2 g (yield 24%) of the desired product as a brown liquid.

Workup

  1. extractionThe reaction mixture was extracted with ethyl acetate
  2. custompurified by column chromatography

Sources & evidence

ORD record
ord-370df2090c1a48a7b4aad6b20a911855
Source dataset
uspto-grants-1989_06
Patent number
US04838924

Reaction notes

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