HCID 13343709, compound → HCID 13343699, compound

HRID 1154592Notes

Reaction equation

HRID 1154592 reaction equation
[CH3:1][O:2][C:3]1[CH:14]=[CH:13][C:6]2[CH:7]=[C:8]([C:10]([OH:12])=[O:11])[O:9][C:5]=2[C:4]=1[CH3:15]>[OH-].[Na+].[Na].[Hg]>[CH3:1][O:2][C:3]1[CH:14]=[CH:13][C:6]2[CH2:7][CH:8]([C:10]([OH:12])=[O:11])[O:9][C:5]=2[C:4]=1[CH3:15]

Participants

4

Reactant 1

HCID 13343709HCID 13343709, compound

Product 1

HCID 13343699HCID 13343699, compound

Reagents, catalysts & solvents 2

HCID 9837419Sodium amalgamCatalystHCID 14798Sodium HydroxideSolvent

Procedure

To a solution of (16i) (29 g., 0.14 mole) dissolved in aqueous sodium hydroxide (15 g. NaOH is 750 ml. of water) was added 550 g. of 5% sodium amalgam portionwise over a period of 30 minutes. The mixture was stirred for 5 hours and then decanted from the mercury and filtered through Celite. The filtrate was acidified with hydrochloric acid and cooled in an ice bath. There was obtained 26 g. of crude acid after filtering. Recrystallization from methylene chloride/hexane gave pure 2,3-dihydro-6-methoxy-7-methylbenzofuran-2-carboxylic acid, m.p. 142°-143° C. Esterification of this material by the procedure described in Example 35 gave (5i) as an oil. Analysis (C13H16O4) C,H.

Workup

  1. additionwas added 550 g
  2. customdecanted from the mercury
  3. filtrationfiltered through Celite
  4. temperaturecooled in an ice bath
  5. customThere was obtained 26 g
  6. filtrationof crude acid after filtering
  7. customRecrystallization from methylene chloride/hexane

Sources & evidence

ORD record
ord-9615c67c1cad4cf0a361e709d38af7a2
Source dataset
uspto-grants-1984_12
Patent number
US04490384

Reaction notes

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