Water → HCID 13826415, compound

HRID 1906918Notes

Reaction equation

HRID 1906918 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]([Cl:12])[C:9]2[C:4](=[CH:5][C:6]([Cl:13])=[CH:7][CH:8]=2)[C:3]=1[C:14](OC)=[O:15].[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>CCOCC>[Cl:1][C:2]1[CH:11]=[C:10]([Cl:12])[C:9]2[C:4](=[CH:5][C:6]([Cl:13])=[CH:7][CH:8]=2)[C:3]=1[CH2:14][OH:15]

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 13826413HCID 13826413, compoundHCID 21226445Aluminium lithium hydride2×

Product 1

HCID 13826415HCID 13826415, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of methyl 2,4,7-trichloro-1-naphthoate (1.3 g, 4.5 mmoles) in ether (50 ml) was added dropwise (15 minutes) to a well stirred suspension of lithium aluminum hydride (0.25 g, 6 mmoles) in ether (25 ml). After stirring at room temperature for 17 hours the reaction mixture was treated with an additional 0.25 g of lithium aluminum hydride. The mixture was stirred for 3 hours, cooled in an ice-bath, and treated dropwise with 0.5 ml of water, 1.5 ml of 20% (w/v) of aqueous NaOH solution, and 0.5 ml of water. After filtration, the solid was extracted with ether. The combined ether solutions were dried (MgSO4), filtered, and concentrated in vacuo to give 1.0 g of the title compound, mp 107°-112° C.

Workup

  1. stirringAfter stirring at room temperature for 17 hours the reaction mixture
  2. stirringThe mixture was stirred for 3 hours
  3. temperaturecooled in an ice-bath
  4. filtrationAfter filtration
  5. extractionthe solid was extracted with ether
  6. dry with materialThe combined ether solutions were dried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-fa0b128b3c1a4c6ab91038824783906c
Source dataset
uspto-grants-1987_03
Patent number
US04654363

Reaction notes

Loading…