Ethyl Acetate → HCID 12859206, compound

HRID 525395Notes

Reaction equation

HRID 525395 reaction equation
[C:1]1([C:7]([OH:11])([CH3:10])[CH2:8][OH:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.CCOC(C)=O>C(Cl)Cl>[OH:11][C:7]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)([CH3:10])[CH:8]=[O:9]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 978672-Phenylpropane-1,2-diolHCID 159087Triacetoxyperiodinane

Product 1

HCID 12859206HCID 12859206, compoundYield 84,418.398%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-phenylpropane-1,2-diol (300 mg, 1.972 mmol) in DCM (60 mL) was added Dess-Martin periodinane (836 mg, 1.972 mmol) at 0° C. The reaction mixture was then stirred for 2 hours at room temperature. After completion of reaction (monitored by TLC (TLC eluent: 50% EtOAc in petroleum ether, UV active)), the reaction mixture was quenched with saturated NaHCO3 solution and extracted with EtOAc. The combined organic layers were washed with water, saturated NaCl solution and dried over anhydrous Na2SO4. The solvents were removed under reduced pressure providing 2-hydroxy-2-phenylpropanal (250 g) as a colorless liquid, which was used without further purification.

Workup

  1. customthe reaction mixture was quenched with saturated NaHCO3 solution
  2. extractionextracted with EtOAc
  3. washThe combined organic layers were washed with water, saturated NaCl solution
  4. dry with materialdried over anhydrous Na2SO4
  5. customThe solvents were removed under reduced pressure

Sources & evidence

ORD record
ord-c8e57bc2ebd84b2e93d7bcea05c5f62b
Source dataset
uspto-grants-2016_05
Patent number
US09340549B2

Reaction notes

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