Resorcinol → Chromone

HRID 268442Notes

Reaction equation

[C:1]1([CH:8]=[CH:7][CH:6]=[C:4]([OH:5])[CH:3]=1)O.[CH3:9]/[C:10](=C\C)/[C:11](O)=[O:12]>>[O:5]1[C:4]2[CH:3]=[CH:1][CH:8]=[CH:7][C:6]=2[C:11](=[O:12])[CH:10]=[CH:9]1

Participants

Reactant 2

HCID 5054Resorcinol

HCID 125468Tiglic acid

Product 1

HCID 10286Chromone

Procedure

Alternatively, the resorcinol can be reacted with methyl crotonic acid according to the method of Fahrenholtz [J. Am. Chem. Soc. 89 5934 (1967)] to give the benzopyran-4-one which in turn is reacted with a Grignard or other organometallic compound to give the desired benzopyran.

Sources & evidence

ORD record: ord-7a0a52496044423f8371dac6449a8353
Source dataset: uspto-grants-1976_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US03947462

Reaction notes

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