Resorcinol → 1,2-Dihydro-9-hydroxy-1-methyl-7-(3-methyl-2-octyl)-4-oxo4H-thieno-[2,3-c][1] benzopyran

HRID 268118

Reaction equation

HRID 268118 reaction equation
[CH3:1][CH:2]1[CH2:6][S:5][CH:4]([C:7]([O:9][CH3:10])=[O:8])[C:3]1=O.[CH3:12][CH:13]([CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])[CH:14]([C:16]1[CH:17]=C(O)[CH:19]=[C:20]([CH:22]=1)[OH:21])[CH3:15].P(Cl)(Cl)(Cl)=O.C1(C=CC=C(O)C=1)O>C1C=CC=CC=1>[OH:21][C:20]1[C:19]2[C:3]3[CH:2]([CH3:1])[CH2:6][S:5][C:4]=3[C:7](=[O:8])[O:9][C:10]=2[CH:17]=[C:16]([CH:14]([CH:13]([CH3:12])[CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])[CH3:15])[CH:22]=1

Participants

6

Reactant 4

HCID 5054ResorcinolHCID 24813Phosphorus oxychlorideHCID 2581765-(3-Methyloctan-2-yl)benzene-1,3-diolHCID 10487456Methyl tetrahydro-4-methyl-3-oxo-2-thiophenecarboxylate

Product 1

HCID 215199901,2-Dihydro-9-hydroxy-1-methyl-7-(3-methyl-2-octyl)-4-oxo4H-thieno-[2,3-c][1] benzopyran

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

A solution in dry benzene of equimolar amounts of methyl 4-methyl-3-oxo-tetrahydrothiophene-2-carboxylate and 5-(3-methyl-2-octyl) resorcinol plus phosphorous oxychloride (5 ml. of benzene/g. of the resorcinol) was warmed for 13 days at 35°-37°C. in an oil bath. Most of the benzene and HCl were removed at reduced pressure, and the dark tarry residue was stirred with ether and water until solution was complete. The ether layer was washed successively with dilute solutions of sodium bicarbonate, sodium hydroxide and sodium carbonate, then with water and saturated sodium chloride. Drying and concentrating the final organic solution left a friable brick-red foamy solid.

Workup

  1. customMost of the benzene and HCl were removed at reduced pressure
  2. washThe ether layer was washed successively with dilute solutions of sodium bicarbonate, sodium hydroxide and sodium carbonate
  3. customDrying
  4. concentrationconcentrating the final organic solution
  5. waitleft a friable brick-red foamy solid

Sources & evidence

ORD record
ord-a079d58fdd594ec28413d3cb891bd874
Source dataset
uspto-grants-1976_03
Patent number
US03946111

Linked notes

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