4-Phenylbutyric Acid → 4-Phenylbutanal

HRID 1796863Notes

Reaction equation

HRID 1796863 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][C:10](O)=[O:11])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.CNOC.Cl.CN(C)CCCN=C=NCC.ON1C2C=CC=CC=2N=N1.CN1CCOCC1.[H-].[Al+3].[Li+].[H-].[H-].[H-].OS([O-])(=O)=O.[Na+]>ClCCl.C(OCC)C>[C:1]1([CH2:7][CH2:8][CH2:9][CH:10]=[O:11])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

10

Reactant 7

HCID 47754-Phenylbutyric AcidHCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 516919Sodium BisulfateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 21226445Aluminium lithium hydride

Product 1

HCID 290304-Phenylbutanal

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent2×HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 4-phenylbutyric acid (1.64 g, 10.0 mmol), N,O-dimethyl hydroxylamine hydrochloride (1.58 g, 16 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (2.06 g, 10.7 mmol), 1-hydroxybenzotriazole (1.56 g, 11.6 mmol), and N-methylmorpholine (2.8 mL, 26 mmol) in dichloromethane (40 mL) at room temperature was stirred for 16 hours, diluted with dichloromethane, washed sequentially with aqueous NaHCO3, brine, 10% KHSO4, and brine, dried (MgSO4), filtered, and concentrated. A mixture of the concentrate and lithium aluminum hydride (9.0 mmol, 1 equiv.) in diethyl ether (49 mL) at room temperature was stirred for 90 minutes, treated with 1M NaHSO4, diluted with diethyl ether, washed sequentially with 10% KHSO4, and brine, dried (MgSO4), filtered, and concentrated to provide the desired product. MS (ESI) m/e 148 (M+H)+.

Workup

  1. washwashed sequentially with aqueous NaHCO3, brine, 10% KHSO4, and brine
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. additionA mixture of the
  6. concentrationconcentrate
  7. washwashed sequentially with 10% KHSO4, and brine
  8. dry with materialdried (MgSO4)
  9. filtrationfiltered
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-f3ffc1b2365449d1ae13a8eef187768f
Source dataset
uspto-grants-2006_04
Patent number
US07030262B2

Reaction notes

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