Benzeneheptanol → 7-Phenylheptanal

HRID 445390Notes

Reaction equation

HRID 445390 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][OH:14])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>C(Cl)Cl>[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH:13]=[O:14])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

3

Reactant 1

HCID 154271Benzeneheptanol

Product 1

HCID 148400647-Phenylheptanal

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 7-phenylheptan-1-ol (5 g) in CH2Cl2 (25 mL) was added to a suspension of 1,1,1-tris(acetyloxy)1,1-dihydro-1,2-benziodoxol-3-(1H)-one (Dess-Martin periodinane) in CH2Cl2 (25 mL) dropwise with ice-bath cooling. The cooling bath was removed after addition was complete and the resulting mixture was stirred at room temperature for 3 h. After addition of a solution of Na2S2O3 (44 g) in saturated NaHCO3, (35 mL), the resulting mixture was stirred for 45 min and the layers were separated. The aqueous layer was extracted twice with CH2Cl2, and the combined organic phases were washed with water, dried over Na2SO4 and concentrated to yield 7-phenylheptanal as an oil, which was used in the next step without further purification.

Workup

  1. temperaturecooling
  2. customThe cooling bath was removed
  3. additionafter addition
  4. additionAfter addition of a solution of Na2S2O3 (44 g) in saturated NaHCO3, (35 mL)
  5. stirringthe resulting mixture was stirred for 45 min
  6. customthe layers were separated
  7. extractionThe aqueous layer was extracted twice with CH2Cl2
  8. washthe combined organic phases were washed with water
  9. dry with materialdried over Na2SO4
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-55b3c23cfc9e4e8eb37c1782670c5db9
Source dataset
uspto-grants-2013_07
Patent number
US08476302B2

Reaction notes

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