Acetone → 4-(2,3-Dihydroxypropoxy)benzaldehyde

HRID 2390532Notes

Reaction equation

HRID 2390532 reaction equation
C([O:4][C:5]1[CH:12]=[CH:11][C:8]([CH:9]=[O:10])=[CH:7][CH:6]=1)C=C.C[N+]1([O-])CC[O:17]CC1.[CH3:21][C:22]([CH3:24])=[O:23]>O.C(O)(C)(C)C.CC(=O)OCC.O=[Os](=O)(=O)=O>[OH:23][CH:22]([CH2:24][OH:17])[CH2:21][O:4][C:5]1[CH:12]=[CH:11][C:8]([CH:9]=[O:10])=[CH:7][CH:6]=1

Participants

8

Reactant 3

HCID 180AcetoneHCID 82029Methyl morpholine oxideHCID 959424-(Allyloxy)benzaldehyde

Product 1

HCID 166558484-(2,3-Dihydroxypropoxy)benzaldehyde

Reagents, catalysts & solvents 4

HCID 30318Osmium TetroxideCatalystHCID 962WaterSolventHCID 6386tert-ButanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-allyloxybenzaldehyde (1.0 g, 6.17 mmol) in acetone (40 mL) and water (5 mL) is added a 2.5% solution of OsO4 in tert. butanol (1.25 mL) followed by N-methyl morpholine-N-oxide (867 mg, 7.4 mmol). The pale yellow solution is stirred at rt for 6 h, diluted with EA (250 mL) and washed with 10% aq. citric acid solution (100 mL) and water (2×100 mL). The washings are extracted with EA (150 mL). The combined organic extracts are concentrated and purified by column chromatography on silica gel to give the title compound (731 mg) as a turbid oil. The title compound reversibly polymerizes upon standing. LC-MS: tR=0.58 min, [M+1+CH3CN]+=238.

Workup

  1. washwashed with 10% aq. citric acid solution (100 mL) and water (2×100 mL)
  2. extractionThe washings are extracted with EA (150 mL)
  3. concentrationThe combined organic extracts are concentrated
  4. custompurified by column chromatography on silica gel

Sources & evidence

ORD record
ord-ceeb7b3f6d454682b52c86f482130755
Source dataset
uspto-grants-2012_09
Patent number
US08273779B2

Reaction notes

Loading…