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

HRID 268119Notes

Reaction equation

HRID 268119 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].[CH3:18][C:19]1([CH3:30])[S:23][CH:22]([C:24](OCC)=[O:25])[C:21](=O)[CH2:20]1>C(O)C>[CH3:18][C:19]1([CH3:30])[S:23][C:22]2[C:24](=[O:25])[O:10][C:9]3[CH:11]=[C:5]([CH:3]([CH:2]([CH3:1])[CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])[CH3:4])[CH:6]=[C:7]([OH:12])[C:8]=3[C:21]=2[CH2:20]1

Participants

4

Reactant 2

HCID 2581765-(3-Methyloctan-2-yl)benzene-1,3-diolHCID 12716257Ethyl 5,5-dimethyl-3-oxothiolane-2-carboxylate

Product 1

HCID 215200041,2-Dihydro-2,2-dimethyl-9-hydroxy-7-(3-methyl-2-octyl)-4-oxo-4H-thieno-[2,3-c][1] benzopyran

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To 100 ml. of ethanol was added 6.2 g. of 5-(3-methyl-2-octyl)resorcinol and 6.2 g. of ethyl 5,5-dimethyl-3-oxotetrahydrothiophene-2-carboxylate. The mixture was cooled in ice and hydrogen chloride was bubbled in for one-half hour. The mixture was stoppered and held at room temperature for 3 days. It was then concentrated and ether added, extracted with water and then washed with dilute aqueous sodium bicarbonate solution. The etheral solution was dried over magnesium sulfate and concentrated. The product was crystallized from acetonitrile to give 5.0 g., m.p. 155°-163°C.

Workup

  1. temperatureThe mixture was cooled in ice
  2. customhydrogen chloride was bubbled in for one-half hour
  3. concentrationIt was then concentrated
  4. additionether added
  5. extractionextracted with water
  6. washwashed with dilute aqueous sodium bicarbonate solution
  7. dry with materialThe etheral solution was dried over magnesium sulfate
  8. concentrationconcentrated
  9. customThe product was crystallized from acetonitrile
  10. customto give 5.0 g

Sources & evidence

ORD record
ord-098fcb95100841839e3f9fed4f971686
Source dataset
uspto-grants-1976_03
Patent number
US03946111

Reaction notes

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