Diethyl Ether → 2-Ethoxy-6-pentadecyl benzaldehyde

HRID 23777Notes

Reaction equation

HRID 23777 reaction equation
[Cr]([O-])(OCl)(=O)=O.[NH+]1C=CC=CC=1.[CH2:13]([O:15][C:16]1[CH:23]=[CH:22][CH:21]=[C:20]([CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH3:38])[C:17]=1[CH2:18][OH:19])[CH3:14].CCOCC>ClCCl>[CH2:13]([O:15][C:16]1[CH:23]=[CH:22][CH:21]=[C:20]([CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH3:38])[C:17]=1[CH:18]=[O:19])[CH3:14]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 667019242-Ethoxy-6-pentadecyl-benzyl alcoholHCID 178526120HCID 178526120, compound

Product 1

HCID 225745702-Ethoxy-6-pentadecyl benzaldehydeYield 83.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a 250 mL round bottom flask fitted with a reflux condenser, was added pyridinium chloro chromate (PCC) (16.1 g, 75 mmol) in anhydrous dichloromethane (100 mL). 2-Ethoxy-6-pentadecyl-benzyl alcohol (18.1 g, 50 mmol) in dichloromethane (10 mL) was added in one portion to the magnetically stirred solution. After 1.5 hr dry ether (100 mL) was added and the supernatant decanted from the black gum. The insoluble residue was washed thoroughly with diethyl ether (3×25 mL), where upon it became black granular solid. The organic solution was passed through a short pad of celite, and the solvent was removed by distillation to obtain brownish low melting solid (Yield: 15 g).

Workup

  1. customTo a 250 mL round bottom flask fitted with a reflux condenser
  2. customthe supernatant decanted from the black gum
  3. washThe insoluble residue was washed thoroughly with diethyl ether (3×25 mL), where upon it
  4. customthe solvent was removed by distillation

Sources & evidence

ORD record
ord-70ca60ef1c224240974ba1e40c7d798f
Source dataset
uspto-grants-2005_02
Patent number
US06852742B2

Reaction notes

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