Hydrochloric Acid → HCID 14579757, compound

HRID 1607294Notes

Reaction equation

HRID 1607294 reaction equation
C([O:4][C:5]1[C:10]2[C:11]([CH3:20])=[C:12]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[O:13][C:9]=2[C:8]([Cl:21])=[CH:7][C:6]=1[CH2:22][CH2:23][CH3:24])(=O)C.[OH-].[Na+].Cl>CO>[Cl:21][C:8]1[C:9]2[O:13][C:12]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[C:11]([CH3:20])[C:10]=2[C:5]([OH:4])=[C:6]([CH2:22][CH2:23][CH3:24])[CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 14579756HCID 14579756, compound

Product 1

HCID 14579757HCID 14579757, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 4-acetoxy-7-chloro-3-methyl-2-phenyl-5-propylbenzofuran (Step c) (1.5 g, 4.6 mmol), methanol (75 mL) and 3N sodium hydroxide (10 mL) was heated to obtain a solution which was then stirred at room temperature for 2 hours. The mixture was acidified with 1N hydrochloric acid (100 mL) and extracted with diethyl ether. The ether extracts were dried (MgSO4), filtered and concentrated. The residue was slurried with hexane, filtered and washed with hexane to obtain the title compound, m.p. 102°-104° C.

Workup

  1. temperaturewas heated
  2. customto obtain a solution which
  3. extractionextracted with diethyl ether
  4. dry with materialThe ether extracts were dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. filtrationfiltered
  8. washwashed with hexane

Sources & evidence

ORD record
ord-04afd7017e9d42b1a89ea3f7fd435c9f
Source dataset
uspto-grants-1989_09
Patent number
US04863958

Reaction notes

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