4-Benzyloxy-1-butanol → 4-Benzyloxybutanal

HRID 376136Notes

Reaction equation

HRID 376136 reaction equation
[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1.[CH2:12]([O:19][CH2:20][CH2:21][CH2:22][CH2:23][OH:24])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>ClCCl>[CH2:12]([O:19][CH2:20][CH2:21][CH2:22][CH:23]=[O:24])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 5622124-Benzyloxy-1-butanolHCID 178418287HCID 178418287, compound

Product 1

HCID 2315594-Benzyloxybutanal

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

36.6 g (170 mmol) of pyridinium chlorochromate are placed at room temperature in 120 ml of dichloromethane under N2, and a solution of 20.4 g (113 mmol) of 4-benzyloxybutanol in 20 ml of dichloromethane is added. The reaction mixture rapidly becomes dark and the reaction is slightly exothermic. The reaction mixture is stirred at room temperature for 31/2 hours. The supernatant dichloromethane phase is decanted off and concentrated by evaporation in a rotary evaporator. The residue is filtered over 100 g of silica gel. The product fractions are concentrated by evaporation in a rotary evaporator and distilled under a high vacuum over a 10 cm Vigreux column. 4-benzyloxybutanal is obtained, b.p.0.1 =72°-73°.

Workup

  1. customThe supernatant dichloromethane phase is decanted off
  2. concentrationconcentrated by evaporation in a rotary evaporator
  3. filtrationThe residue is filtered over 100 g of silica gel
  4. concentrationThe product fractions are concentrated by evaporation in a rotary evaporator
  5. distillationdistilled under a high vacuum over a 10 cm Vigreux column

Sources & evidence

ORD record
ord-57466193e0174ca9916aeeb67f750b1a
Source dataset
uspto-grants-1996_01
Patent number
US05488140

Reaction notes

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