Water → HCID 22388433, compound

HRID 1072895Notes

Reaction equation

HRID 1072895 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl:7][C:8]1[CH:19]=[C:18]([O:20][CH:21]([CH3:23])[CH3:22])[CH:17]=[CH:16][C:9]=1[C:10](OC(C)C)=[O:11].O.[OH-].[Na+]>CCOCC>[Cl:7][C:8]1[CH:19]=[C:18]([O:20][CH:21]([CH3:23])[CH3:22])[CH:17]=[CH:16][C:9]=1[CH2:10][OH:11]

Participants

6

Reactant 4

HCID 962Water3×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 223877681-Methylethyl 2-chloro-4-(1-methylethoxy)benzoate

Product 1

HCID 22388433HCID 22388433, compoundYield 97.2%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

Lithium aluminum hydride (100 mg) was added to a solution of isopropyl 2-chloro-4-isopropoxybenzoate (675 mg) in ether (6.8 ml) and the mixture was stirred for 2 hr. To the reaction mixture were dropwise added successively water (0.8 ml), a 1N aqueous sodium hydroxide solution (0.8 ml) and water (2.4 ml) under ice-cooing, and the mixture was stirred for 30 min at room temperature. Then ether and water were added and the organic layer was separated. The resulting product was extracted with ether from the aqueous layer. The organic layers were combined, washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated to give the objective compound (513 mg) as a brown oil.

Workup

  1. customthe organic layer was separated
  2. extractionThe resulting product was extracted with ether from the aqueous layer
  3. washwashed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated

Sources & evidence

ORD record
ord-e1375b66bef3409db7c58bf333ba7bc0
Source dataset
uspto-grants-2005_06
Patent number
US06911469B2

Reaction notes

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