Olivetol → 1,2-dihydro-9-hydroxy-2-methyl-7-n-pentyl-4-oxo-4H-thieno[2,3-c][1] benzopyran

Reaction equation

[CH2:1]([C:6]1[CH:7]=[C:8]([OH:13])[CH:9]=[C:10]([CH:12]=1)[OH:11])[CH2:2][CH2:3][CH2:4][CH3:5].[CH3:14][CH:15]1[S:19][CH:18]([C:20](OC)=[O:21])[C:17](=O)[CH2:16]1>>[OH:13][C:8]1[C:9]2[C:17]3[CH2:16][CH:15]([CH3:14])[S:19][C:18]=3[C:20](=[O:21])[O:11][C:10]=2[CH:12]=[C:6]([CH2:1][CH2:2][CH2:3][CH2:4][CH3:5])[CH:7]=1

Participants

Reactant 2

HCID 10377Olivetol

HCID 12914976Methyl 5-methyl-3-oxo-tetrahydrothiophene-2-carboxylate

Product 1

HCID 215535591,2-dihydro-9-hydroxy-2-methyl-7-n-pentyl-4-oxo-4H-thieno[2,3-c][1] benzopyranYield 62%

Procedure

5-n-Pentyl resorcinol is reacted with methyl 5-methyl-3-oxo-tetrahydrothiophene-2-carboxylate to produce 1,2-dihydro-9-hydroxy-2-methyl-7-n-pentyl-4-oxo-4H-thieno[2,3-c][1] benzopyran, m.p. 188°-190°C, in 62% yield.

Sources & evidence

ORD record: ord-1de5cadc2bf5423f9b71531a1180b1ad
Source dataset: uspto-grants-1976_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US03946111

Reaction notes

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