Hydrochloric Acid → 1,2-Dihydro-10-hydroxy-8-(3-methyl-2-octyl)-5-oxo-3H,5H-thiopyrano[2,3-c][1]benzopyran

HRID 1580848Notes

Reaction equation

HRID 1580848 reaction equation
[CH3:1][CH:2]([CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])[CH:3]([C:5]1[CH:6]=[C:7]([OH:12])[CH:8]=[C:9]([CH:11]=1)[OH:10])[CH3:4].O=[C:19]1[CH2:24][CH2:23][CH2:22][S:21][CH:20]1[C:25](OC)=[O:26].Cl>C(O)C>[OH:10][C:9]1[C:8]2[C:19]3[CH2:24][CH2:23][CH2:22][S:21][C:20]=3[C:25](=[O:26])[O:12][C:7]=2[CH:6]=[C:5]([CH:3]([CH:2]([CH3:1])[CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])[CH3:4])[CH:11]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 2581765-(3-Methyloctan-2-yl)benzene-1,3-diolHCID 18379299Methyl 3-oxotetrahydrothiopyran-2-carboxylate

Product 1

HCID 214339161,2-Dihydro-10-hydroxy-8-(3-methyl-2-octyl)-5-oxo-3H,5H-thiopyrano[2,3-c][1]benzopyran

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 14.2 g. (0.06 mole) of 5-(3-methyl-2-octyl)resorcinol and 11.1 g. (0.063 mole) of methyl 3-oxo-2,3,4,5-tetrahydro-6H-thiopyran-2-carboxylate in 90 ml. of absolute ethanol was cooled in an ice-salt bath and saturated with anhydrous hydrogen chloride. After standing for 2 days at room temperature, the ethanol was removed on a rotary evaporator. The residue was dissolved in ether, washed with sodium bicarbonate solution and dried over sodium sulfate. Evaporation of the solvent gave 28.0 g. of residue which was chromatographed using activated magnesium silicate (60-100 mesh) and graded methanol/chloroform solvent mixtures. A total of 10 g. of crude solid was obtained from the 1% methanol/chloroform fractions. The material was recrystallized twice from ethyl acetate/hexane to give 8.5 g. (40%) colorless crystals, m.p. 131°-133°C. The proposed structure was confirmed by IR and NMR spectra.

Workup

  1. customthe ethanol was removed on a rotary evaporator
  2. dissolutionThe residue was dissolved in ether
  3. washwashed with sodium bicarbonate solution
  4. dry with materialdried over sodium sulfate
  5. customEvaporation of the solvent
  6. customgave 28.0 g
  7. customof residue which was chromatographed
  8. customof crude solid was obtained from the 1% methanol/chloroform fractions
  9. customThe material was recrystallized twice from ethyl acetate/hexane
  10. customto give 8.5 g

Sources & evidence

ORD record
ord-14b1f31431054cbeb417f5e730bc7743
Source dataset
uspto-grants-1976_01
Patent number
US03934024

Reaction notes

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