5-Phenyl-1-pentanol → Benzenepentanal

HRID 1107118Notes

Reaction equation

HRID 1107118 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][OH:12])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Na+].[Br-].CC1(C)N([O])C(C)(C)CCC1.[O-]Cl.[Na+].C([O-])(O)=O.[Na+]>CCOC(C)=O.O.C1(C)C=CC=CC=1>[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10][CH:11]=[O:12])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

9

Reactant 5

HCID 615235-Phenyl-1-pentanolHCID 253881Sodium BromideHCID 516892Sodium BicarbonateHCID 2724126TempoHCID 23665760Sodium Hypochlorite

Product 1

HCID 561886Benzenepentanal

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 5-phenylpentanol (5 g, 30.4 mmol), NaBr (3.2 g, 31.3 mmol), and TEMPO® (48 mg, 0.3 mmol) in EtOAc (60 mL), toluene (60 mL), and water (9 mL), cooled to 0° C., is added portionwise (50 mL) over 30 minutes a solution containing NaOCl (0.35 M in H2O, 287 mL, 100.4 mmol) and NaHCO3 (22.2 g, 264.8 mmol). The reaction is quenched by the addition of EtOH (10 mL). The biphasic mixture is separated and the organic phase is washed with aqueous Na2S2O3 (2×100 mL), brine (100 mL), dried over anhydrous MgSO4, filtered and concentrated to afford crude 5-phenylpentanal which is homogeneous by TLC analysis [hexane/EtOAc, 4:1, Rf (5-phenylpentanol)=0.30; Rf (5-phenylpentanal)=0.65] and used without further purification.

Workup

  1. additionis added portionwise (50 mL) over 30 minutes a solution
  2. customThe reaction is quenched by the addition of EtOH (10 mL)
  3. customThe biphasic mixture is separated
  4. washthe organic phase is washed with aqueous Na2S2O3 (2×100 mL), brine (100 mL)
  5. dry with materialdried over anhydrous MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-eea9fc6b1e4c4fef8c816d69a7790916
Source dataset
uspto-grants-2000_05
Patent number
US06057369

Reaction notes

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