Hydrochloric Acid → 1,2-Dihydro-9-hydroxy-7-(3-methyl-2-octyl)-4-oxo-4H-thieno[2,3-c][1]benzopyran

HRID 1282852Notes

Reaction equation

HRID 1282852 reaction equation
CO[C:3]([CH:5]1[C:9](=O)[CH2:8][S:7][CH2:6]1)=O.[CH3:11][CH:12]([CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])[CH:13]([C:15]1[CH:16]=[C:17]([OH:22])C=[C:19]([CH:21]=1)[OH:20])[CH3:14].Cl.[CH2:29]([OH:31])C>>[OH:22][C:17]1[C:3]2[C:5]3[CH2:9][CH2:8][S:7][C:6]=3[C:29](=[O:31])[O:20][C:19]=2[CH:21]=[C:15]([CH:13]([CH:12]([CH3:11])[CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])[CH3:14])[CH:16]=1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 984243-Thiophenecarboxylic acid, tetrahydro-4-oxo-, methyl esterHCID 2581765-(3-Methyloctan-2-yl)benzene-1,3-diol

Product 1

HCID 214339001,2-Dihydro-9-hydroxy-7-(3-methyl-2-octyl)-4-oxo-4H-thieno[2,3-c][1]benzopyran

Procedure

A solution of 20 g. (0.125 mole) of methyl-4-oxo-2,3,4,5-tetrahydrothiophene-3-carboxylate and 32 g. (0.135 mole of 5-(3-methyl-2-octyl)resorcinol in 200 ml. of absolute ethanol was cooled in an ice-salt bath and saturated with anhydrous hydrogen chloride. The reaction mixture was allowed to stand at room temperature for 72 hours and the solid which formed was removed by filtration. Recrystallization from ethanol gave 16 g. (37%) m.p. 165°-166°C. The structure was confirmed by infrared and nuclear magnetic resonance spectra.

Workup

  1. customthe solid which formed
  2. customwas removed by filtration
  3. customRecrystallization from ethanol
  4. customgave 16 g

Sources & evidence

ORD record
ord-bd84788681894d568ae26b156b2bfe7a
Source dataset
uspto-grants-1976_08
Patent number
US03972880

Reaction notes

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