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

HRID 268120Notes

Reaction equation

[CH3:1][C:2]1([CH3:13])[S:6][CH:5]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[C:4](=O)[CH2:3]1.[CH2:14]([C:19]1[CH:20]=C(O)C=[C:23]([CH:25]=1)[OH:24])[CH2:15][CH2:16][CH2:17][CH3:18]>>[CH3:1][C:2]1([CH3:13])[S:6][C:5]2[C:7](=[O:8])[O:9][C:10]3[CH:20]=[C:19]([CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[CH:25]=[C:23]([OH:24])[C:11]=3[C:4]=2[CH2:3]1

Participants

Reactant 2

HCID 10377Olivetol

HCID 12716257Ethyl 5,5-dimethyl-3-oxothiolane-2-carboxylate

Product 1

HCID 215535651,2-dihydro-2,2-dimethyl-9-hydroxy-7-n-pentyl-4-oxo-4H-thieno-[2,3-c][1] benzopyranYield 72.5%

Procedure

Ethyl 5,5-dimethyl-3-oxo-tetrahydrothiophene-2-carboxylate was reacted with 5-n-pentyl resorcinol following a procedure similar to that of Example 3-C to produce 1,2-dihydro-2,2-dimethyl-9-hydroxy-7-n-pentyl-4-oxo-4H-thieno-[2,3-c][1] benzopyran in a 72.5% yield, m.p. 203°-206°C.

Sources & evidence

ORD record: ord-8469ca5d080e4fddb719895d1063a686
Source dataset: uspto-grants-1976_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US03946111

Reaction notes

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