Water → 4-(2,3-Dihydroxypropoxy)-3-chlorobenzaldehyde

HRID 38719

Reaction equation

HRID 38719 reaction equation
[CH2:1]([O:4][C:5]1[CH:12]=[CH:11][C:8]([CH:9]=[O:10])=[CH:7][C:6]=1[Cl:13])[CH:2]=[CH2:3].[OH2:14].C[N+]1([O-])CC[O:19]CC1>CC(C)=O.CC(=O)OCC.O=[Os](=O)(=O)=O.C(O)(C)(C)C>[OH:14][CH:2]([CH2:3][OH:19])[CH2:1][O:4][C:5]1[CH:12]=[CH:11][C:8]([CH:9]=[O:10])=[CH:7][C:6]=1[Cl:13]

Participants

8

Reactant 3

HCID 962WaterHCID 82029Methyl morpholine oxideHCID 47700363-Chloro-4-(prop-2-en-1-yloxy)benzaldehyde

Product 1

HCID 798396484-(2,3-Dihydroxypropoxy)-3-chlorobenzaldehyde

Reagents, catalysts & solvents 4

HCID 6386tert-ButanolCatalystHCID 30318Osmium TetroxideCatalystHCID 180AcetoneSolventHCID 8857Ethyl AcetateSolvent

Procedure

The above 4-allyloxy-3-chloro-benzaldehyde (5.37 g, 27.3 mmol) is dissolved in acetone (100 mL) and water (10 mL) and treated with a 2.5% solution of OsO4 in tert.-butanol (1.71 mL, 0.137 mmol OsO4). N-methyl morpholine-N-oxide (3.87 g, 32.8 mmol) is added and the reaction mixture is stirred at rt for 20 h before it is diluted with EA (300 mL) and washed with 10% aq. citric acid solution (200 mL) and water (2×150 mL). The washings are extracted with EA (300 mL) and the combined organic extracts are dried over MgSO4, filtered and concentrated to furnish the title compound (6.02 g) as beige foam which was used in the following steps without further purification. LC: tR=0.67 min.

Workup

  1. washwashed with 10% aq. citric acid solution (200 mL) and water (2×150 mL)
  2. extractionThe washings are extracted with EA (300 mL)
  3. dry with materialthe combined organic extracts are dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-a50a026ccdeb406389225a2375678e72
Source dataset
uspto-grants-2013_09
Patent number
US08524752B2

Linked notes

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