Hexane → 2-(4-Bromophenyl)propane-1,3-diol

HRID 515457

Reaction equation

HRID 515457 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:14](OCC)=[O:15])[C:9](OCC)=[O:10])=[CH:4][CH:3]=1.[H-].C([Al+]CC(C)C)C(C)C.CCCCCC.C(C(C(C([O-])=O)O)O)([O-])=O.[Na+].[K+]>CCOCC>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([CH2:14][OH:15])[CH2:9][OH:10])=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 8058HexaneHCID 9855836Potassium sodium tartarateHCID 10519382Diethyl 4-bromophenylmalonateHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 218667012-(4-Bromophenyl)propane-1,3-diolYield 37.4%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of diethyl 2-(4-bromophenyl)malonate (18.1 g, 57.5 mmol) in ether (285 ml) was added 0.98M-diisobutylaluminium hydride in hexane (259 ml, 254 mmol) at 0° C. under nitrogen atmosphere. The resulting mixture was stirred at 0° C. for 4 hours. Aqueous potassium sodium tartrate (0.57M, 500 ml) was added to the reaction mixture for quenching the aluminum reagent and the mixture was stirred for 14 hours. The organic layer was extracted with ethyl acetate and dried over sodium sulfate. After concentration, the residue was purified by silica gel column chromatography (eluant: hexane/ethyl acetate=40/60 to ethyl acetate only) to afford 2-(4-bromophenyl)propane-1,3-diol as white solid (4.97 g, 37%).

Workup

  1. customfor quenching the aluminum reagent
  2. stirringthe mixture was stirred for 14 hours
  3. extractionThe organic layer was extracted with ethyl acetate
  4. dry with materialdried over sodium sulfate
  5. concentrationAfter concentration
  6. customthe residue was purified by silica gel column chromatography (eluant

Sources & evidence

ORD record
ord-073ca934b9104bed9e97062c70542276
Source dataset
uspto-grants-2015_08
Patent number
US09108957B2

Linked notes

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