Isopentadecan-1-ol → 13-methyltetradecanal

HRID 2215874Notes

Reaction equation

HRID 2215874 reaction equation
[CH3:1][CH:2]([CH3:16])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][OH:15]>ClCCl>[CH3:1][CH:2]([CH3:16])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH:14]=[O:15]

Participants

3

Reactant 1

HCID 94094Isopentadecan-1-ol

Product 1

HCID 1108550713-methyltetradecanalYield 51%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Chloro-chromic pyridine (161.6 g, 0.75 mole) and 450 ml dichloromethane were added to a flask. With stirring, 150 ml dichloromethane solution of 13-methyl-1-tetradecanol (114 g, 0.50 mole) was slowly added to the flask and stirring continued for 1.5 hours at room temperature. Let the mixture stand and separate into two phases. Decant upper phase and wash the remainder with 100 ml diethyl ether. Combine all liquid and wash sequentially with saturated NaCl, 10% HCl, and saturated NaCl solution with 5% NaHCO3. Desiccate with anhydrous CaCl2 and remove solvent by evaporation to yield 13-methyl-tetradecanaldehyde (57.6 g, yield rate 51%).

Workup

  1. stirringstirring
  2. customseparate into two phases
  3. customDecant upper phase
  4. washwash the remainder with 100 ml diethyl ether
  5. washCombine all liquid and wash sequentially with saturated NaCl, 10% HCl, and saturated NaCl solution with 5% NaHCO3
  6. customDesiccate with anhydrous CaCl2 and remove solvent
  7. customby evaporation

Sources & evidence

ORD record
ord-d903c0b942024688b9098a2f5c07d6cf
Source dataset
uspto-grants-2006_09
Patent number
US07109364B2

Reaction notes

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