Hydrochloric Acid → HCID 21568956, compound

HRID 1579626Notes

Reaction equation

HRID 1579626 reaction equation
[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]([CH:17]([CH3:19])[CH3:18])[C:5](=[O:20])[C:4]=2[C:3]=1[CH3:21].[H-].[Na+].[CH3:24]I.[OH-].[Na+].Cl>CN(C)C=O.O>[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][C:6]([CH3:24])([CH:17]([CH3:18])[CH3:19])[C:5](=[O:20])[C:4]=2[C:3]=1[CH3:21]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 6328Methyl iodideHCID 14798Sodium HydroxideHCID 24758Sodium hydrideHCID 21568950HCID 21568950, compound

Product 1

HCID 21568956HCID 21568956, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

A solution of 4,5-dimethyl-6-oxo-7-isopropyl1,2,7,8-tetrahydro-6H-indeno[5,4-b]furan-2-carboxylic acid (0.01 mole) in dimethylformamide (50 ml.) at 15°C. is treated with sodium hydride (50% dispersion in mineral oil, (0.-25 mole). The solution is warmed to 50°C., cooled to 25°C., treated with methyl iodide (0.025 mole) then warmed to 50°C. Thereafter, water (50 ml.) and 10 N sodium hydroxide (2 ml.) are added; the reaction is heated at 95°C. for 0.5 hours then poured into cold 1.0N hydrochloric acid to afford 4,5,7-trimethyl-6-oxo-7-isopropyl-1,2,7,8-tetrahydro-6H-indeno[5,4-b]furan-2-carboxylic acid.

Workup

  1. temperaturecooled to 25°C.
  2. temperaturethen warmed to 50°C
  3. temperaturethe reaction is heated at 95°C. for 0.5 hours

Sources & evidence

ORD record
ord-b832a26e8c7041b49bd13754c7d168e2
Source dataset
uspto-grants-1976_01
Patent number
US03931239

Reaction notes

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