Sodium Acetate → Methyl 4-(4-oxobutyl)benzoate

HRID 2259444Notes

Reaction equation

HRID 2259444 reaction equation
[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1.C([O-])(=O)C.[Na+].[OH:17][CH2:18][CH2:19][CH2:20][CH2:21][C:22]1[CH:31]=[CH:30][C:25]([C:26]([O:28][CH3:29])=[O:27])=[CH:24][CH:23]=1>C(Cl)Cl.C(OCC)C>[C:26]([C:25]1[CH:30]=[CH:31][C:22]([CH2:21][CH2:20][CH2:19][CH:18]=[O:17])=[CH:23][CH:24]=1)([O:28][CH3:29])=[O:27]

Participants

6

Reactant 3

HCID 517045Sodium AcetateHCID 14603109Methyl 4-(4-hydroxybutyl)benzoateHCID 178418287HCID 178418287, compound

Product 1

HCID 9859111Methyl 4-(4-oxobutyl)benzoate

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a mixture of 4.19 g (1.5 eq) of pyridinium chlorochromate and 1.76 g (1.0 eq) of sodium acetate in 100 mL of dry methylene chloride are added, under nitrogen and with stirring, 2.70 g (1.0 eq) of methyl 4-(4-hydroxybutyl)benzoate in 50 mL of dry methylene chloride. The reaction mixture is stirred 12 hours, diluted with diethyl ether, and filtered. After concentration at reduced pressure, the residue is distilled under vacuum to yield 4-(4-carbomethoxyphenyl)butanal as an oil, b.p. 131° C. at <1 torr; IR (film) ν max 2950, 2720, 1722, 1612, 1285, and 1110 cm-1 ; 1H NMR (CDC13) delta 9.77 (m, 1H, --CHO), 7.98 (d, J=9 Hz, 2H, Ar), 7.24 (d, J=8.2 Hz, 2H, Ar), 3.90 (s, 3H, --CH3), 2.72 (t, 2H, benzyl), 2.47 (m, 2H, --CH2CHO), 1.95 (m, 2H, --CH2).

Workup

  1. additionare added, under nitrogen
  2. stirringThe reaction mixture is stirred 12 hours
  3. filtrationfiltered
  4. concentrationAfter concentration at reduced pressure
  5. distillationthe residue is distilled under vacuum

Sources & evidence

ORD record
ord-db650ca398624d12add5ce87fb711201
Source dataset
uspto-grants-1995_12
Patent number
US05473071

Reaction notes

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