5-(3-Methyloctan-2-yl)benzene-1,3-diol → 1,2-Dihydro-9-hydroxy-2-methyl-7-(3-methyl-2-octyl)-4-oxo-4H-thieno-[2,3-c][1]benzopyran

HRID 268121

Reaction equation

HRID 268121 reaction equation
[CH3:1][CH:2]1[S:6][CH:5]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[C:4](=O)[CH2:3]1.[CH3:13][CH:14]([CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])[CH:15]([C:17]1[CH:18]=C(O)C=[C:21]([CH:23]=1)[OH:22])[CH3:16]>C(O)C>[OH:22][C:21]1[C:11]2[C:4]3[CH2:3][CH:2]([CH3:1])[S:6][C:5]=3[C:7](=[O:8])[O:9][C:10]=2[CH:18]=[C:17]([CH:15]([CH:14]([CH3:13])[CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])[CH3:16])[CH:23]=1

Participants

4

Reactant 2

HCID 2581765-(3-Methyloctan-2-yl)benzene-1,3-diolHCID 12716255Ethyl 5-methyl-3-oxo-tetrahydrothiophene-2-carboxylate

Product 1

HCID 215199881,2-Dihydro-9-hydroxy-2-methyl-7-(3-methyl-2-octyl)-4-oxo-4H-thieno-[2,3-c][1]benzopyran

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To 45 ml. of ethanol was added 8.8 g. of crude ethyl 5-methyl-3-oxo-tetrahydrothiophene-2-carboxylate and 5 g. of 5-(3-methyl-2-octyl) resorcinol. The mixture was cooled in ice and hydrogen chloride was bubbled in for onehalf hour. The mixture was stoppered and let stand at room temperature for 3 days. The reaction mixture was concentrated and dissolved in ether. The ether solution was extracted twice with water and once with aqueous sodium bicarbonate solution. The solution was dried over magnesium sulfate and concentrated. The product was crystallized from acetonitrile to give 4.65 g., m.p. 146°-149°C.

Workup

  1. temperatureThe mixture was cooled in ice
  2. customhydrogen chloride was bubbled in for onehalf hour
  3. concentrationThe reaction mixture was concentrated
  4. dissolutiondissolved in ether
  5. extractionThe ether solution was extracted twice with water and once with aqueous sodium bicarbonate solution
  6. dry with materialThe solution was dried over magnesium sulfate
  7. concentrationconcentrated
  8. customThe product was crystallized from acetonitrile
  9. customto give 4.65 g

Sources & evidence

ORD record
ord-4223cd0c4d2048bead90edbf766604c8
Source dataset
uspto-grants-1976_03
Patent number
US03946111

Linked notes

Loading…