Hydrochloric Acid → HCID 21481316, compound

HRID 435772Notes

Reaction equation

HRID 435772 reaction equation
[Cl:1][C:2]1[C:10]([CH3:11])=[C:9]([OH:12])[CH:8]=[C:7]2[C:3]=1[C:4](=[O:18])[C:5]1([CH2:17][CH2:16][CH2:15][CH2:14]1)[C:6]2=[O:13].[H-].COCCO[Al+]OCCOC.[Na+].[H-].Cl>O1CCCC1.C1C=CC=CC=1>[Cl:1][C:2]1[C:10]([CH3:11])=[C:9]([OH:12])[CH:8]=[C:7]2[C:3]=1[CH:4]([OH:18])[C:5]1([CH2:17][CH2:16][CH2:15][CH2:14]1)[CH:6]2[OH:13]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 21481325HCID 21481325, compoundHCID 21584525Sodium bis(2-methoxyethoxy)aluminiumhydride

Product 1

HCID 21481316HCID 21481316, compound

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
25 °C

Procedure

A solution of 4'-chloro-5'-methyl-6'-hydroxyspiro(cyclopentane-1,2'-indan)-1',3'-dione (4.0 g., 0.015 mole) in tetrahydrofuran (100 ml.) is cooled to 15° C. and treated over 5 minutes with a solution of sodium bis-(2-methoxyethoxy)aluminum hydride (10 ml. of a 70% solution in benzene). The reaction is stirred one-half hour at 25° C., cooled to 10° C. and slowly treated with 20% aqueous hydrochloric acid until acidic. The organic phase is evaporated to an oil, dissolved in ether, washed with water, dried over magnesium sulfate and the solvent evaporated affording 4'-chloro-5'-methylspiro(cyclopentane-1,2'-indan)-1',3',6'-triol.

Workup

  1. temperaturecooled to 10° C.
  2. customThe organic phase is evaporated to an oil
  3. dissolutiondissolved in ether
  4. washwashed with water
  5. dry with materialdried over magnesium sulfate
  6. customthe solvent evaporated

Sources & evidence

ORD record
ord-3daf983ece3f4521b530839db6d3a744
Source dataset
uspto-grants-1977_02
Patent number
US04006180

Reaction notes

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