HCID 12741934, compound → HCID 12741935, compound

HRID 1579639Notes

Reaction equation

HRID 1579639 reaction equation
[CH3:1][C:2]1[C:10]2[O:11][C:12]([C:14]([OH:16])=[O:15])=[CH:13][C:9]=2[C:8]2[CH2:7][CH:6]([CH2:17][CH2:18][CH3:19])[C:5](=[O:20])[C:4]=2[C:3]=1[CH3:21]>C(=O)(O)[O-].[Na+].[Na].[Hg]>[CH3:1][C:2]1[C:10]2[O:11][CH:12]([C:14]([OH:16])=[O:15])[CH2:13][C:9]=2[C:8]2[CH2:7][CH:6]([CH2:17][CH2:18][CH3:19])[CH:5]([OH:20])[C:4]=2[C:3]=1[CH3:21]

Participants

4

Reactant 1

HCID 12741934HCID 12741934, compound

Product 1

HCID 12741935HCID 12741935, compound

Reagents, catalysts & solvents 2

HCID 9837419Sodium amalgamCatalystHCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
25 °C

Procedure

A solution of 4,5-dimethyl-6-oxo-7-propyl-7,8-dihydro-6H-indeno[5,4-b]furan-2-carboxylic acid (2.0 g., 0.007 mole) in aqueous sodium bicarbonate (40 ml.) is treated with 1% sodium amalgam (120 g.) and stirred at 25°C. for 18 hours. The mercury is separated and the aqueous phase is acidified with hydrochloric acid affording 2.0 g. (99%) of 4,5-dimethyl-6-hydroxy-7-propyl-1,2,7,8-tetrahydro-6H-indeno[5,4-b]furan-2-carboxylic acid which melts at 161°C. after recrystallization from nitromethane.

Workup

  1. customThe mercury is separated
  2. custom(99%) of 4,5-dimethyl-6-hydroxy-7-propyl-1,2,7,8-tetrahydro-6H-indeno[5,4-b]furan-2-carboxylic acid which melts at 161°C. after recrystallization from nitromethane

Sources & evidence

ORD record
ord-00fa64ae90ae44b1b572542492afd760
Source dataset
uspto-grants-1976_01
Patent number
US03931239

Reaction notes

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