5-Phenyl-1-pentanol → Benzenepentanal

HRID 1107103Notes

Reaction equation

HRID 1107103 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.[Br-].[Na+].CC1(C)N([O])C(C)(C)CCC1.[O-]Cl.[Na+].C([O-])(O)=O.[Na+]>C(O)C.O.C1(C)C=CC=CC=1.CCOC(C)=O>[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

10

Reactant 5

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

Product 1

HCID 561886BenzenepentanalYield 100%

Reagents, catalysts & solvents 4

HCID 702EthanolSolventHCID 962WaterSolventHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

A solution containing 5-phenylpentanol (10 g, 60 mmol), sodium bromide (6.45 g, 63 mmol) and TEMPO (95 mg, 0.6 mmol) in a 7:7:1 mixture of EtOAc, toluene and water (258 mL) is cooled to 0° C. With vigorous stirring, an aqueous NaOCl solution (0.35 M, 571 mL, 200 mmol) saturated with NaHCO3 (43.85 g, 520 mmol) is added in five portions separated by 10 minutes intervals. TLC analysis following the final addition indicated complete reaction. Ethanol (20 mL) is added and the mixture is partitioned between water (500 mL) and EtOAc (500 mL). Aqueous layer is extracted with EtOAc (2×500 mL) and combined organic phases are washed successively with 5% aqueous Na2S2O3 (500 mL), water (200 mL) and brine (200 mL) then dried over MgSO4 and concentrated to afford 5-phenylpentanal as an orange oil which is used without further purification assuming 100% yield. TLC analysis [pet-ether/EtOAc, 9:1, Rf (alcohol)=0.20, Rf (aldehyde)=0.60]. 1H NMR (300 MHz, CDCl3) δ 1.65 (m, 4H), 2.35 (m, 2H), 2.60 (t, 2H), 7.10-7.30 (m, 5H), 9.75 (s, 1H) ppm.

Workup

  1. customseparated by 10 minutes intervals
  2. additionaddition
  3. customreaction
  4. customthe mixture is partitioned between water (500 mL) and EtOAc (500 mL)
  5. extractionAqueous layer is extracted with EtOAc (2×500 mL)
  6. washare washed successively with 5% aqueous Na2S2O3 (500 mL), water (200 mL) and brine (200 mL)
  7. dry with materialthen dried over MgSO4
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-ce1f32c8eb2d4cffa314cb501aade13c
Source dataset
uspto-grants-2000_05
Patent number
US06057369

Reaction notes

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