Hydrochloric Acid → HCID 86744321, compound

HRID 1089566Notes

Reaction equation

HRID 1089566 reaction equation
C(O[C:5]1[C:6]([CH3:24])=[C:7]([CH3:23])[C:8]2[O:12][CH:11](CSC3C=CC=CC=3)[CH2:10][C:9]=2[C:21]=1[CH3:22])(=O)C.[OH-].[Na+].Cl>CO.O>[CH3:22][C:21]1[C:9]2[CH2:10][CH2:11][O:12][C:8]=2[C:7]([CH3:23])=[C:6]([CH3:24])[CH:5]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 14856380HCID 14856380, compound

Product 1

HCID 86744321HCID 86744321, compoundYield 149.7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

To a solution of 5-acetoxy-2-(phenylthiomethyl)-4,6,7-trimethyl-2,3-dihydrobenzofuran [1.2 g (3.5 mmol)] in methanol (8 ml) was added a solution of sodium hydroxide (0.6 g) in water (5 ml). The mixture was heated for one hour under reflux under argon atmosphere. The reaction mixture was, after cooling, diluted with water and, then, neutralized with 2N-HCl and followed by extraction with ethyl acetate. The extract solution was washed with water, and dried, then the solvent was distilled off. The residue was crystallized from isopropyl ether-hexane to obtain 5-hydroxy-2-phenylthiomethyl)-4,6,7-trimethyl-2,3-dihydrobenzofuran (Compound 3) (0.85 g).

Workup

  1. temperatureThe mixture was heated for one hour
  2. temperatureunder reflux under argon atmosphere
  3. temperatureafter cooling
  4. extractionfollowed by extraction with ethyl acetate
  5. washThe extract solution was washed with water
  6. customdried
  7. distillationthe solvent was distilled off
  8. customThe residue was crystallized from isopropyl ether-hexane

Sources & evidence

ORD record
ord-c4cc387ed7a4497b837d579983eb5922
Source dataset
uspto-grants-1990_10
Patent number
US04966973

Reaction notes

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