3-Benzyloxy-1-propanol → 3-(Benzyloxy)propanal

HRID 468480Notes

Reaction equation

HRID 468480 reaction equation
C1C=C[NH+]=CC=1.[O-][Cr](Cl)(=O)=O.[CH2:12]([O:19][CH2:20][CH2:21][CH2:22][OH:23])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>ClCCl>[CH2:12]([O:19][CH2:20][CH2:21][CH:22]=[O:23])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 3479713-Benzyloxy-1-propanolHCID 178418287HCID 178418287, compound

Product 1

HCID 108882613-(Benzyloxy)propanalYield 79%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a suspension of PCC (606 mg, 2.82 mmol) in anhydrous dichloromethane (8 mL) at room temperature under N2 was added a solution of 3-benzyloxy-1-propanol (310 mg, 1.88 mmol) in anhydrous dichloromethane. The reaction mixture was stirred overnight at room temperature, filtrated through Celite, and concentrated. The residue was purified by column chromatography on silica gel (1-10% ethyl acetate/hexanes) to give 3-(benzyloxy)propanal (243 mg, 79%).

Workup

  1. filtrationfiltrated through Celite
  2. concentrationconcentrated
  3. customThe residue was purified by column chromatography on silica gel (1-10% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-b3149696b29149939d55a9d77ec954d4
Source dataset
uspto-grants-2014_01
Patent number
US08623905B2

Reaction notes

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