Acetic Acid → HCID 86677695, compound

HRID 1499764Notes

Reaction equation

HRID 1499764 reaction equation
[Cl:1][C:2]1[C:3]([CH3:18])=[C:4]([CH:14]([OH:17])CO)[C:5]([O:11][CH2:12][CH3:13])=[C:6]([C:8](=[O:10])[CH3:9])[CH:7]=1.C(O)(=O)C.I([O-])(=O)(=O)=O.[Na+]>O1CCCC1.O>[C:8]([C:6]1[C:5]([O:11][CH2:12][CH3:13])=[C:4]([C:3]([CH3:18])=[C:2]([Cl:1])[CH:7]=1)[CH:14]=[O:17])(=[O:10])[CH3:9]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 23667635Sodium periodateHCID 86677696HCID 86677696, compound

Product 1

HCID 86677695HCID 86677695, compoundYield 104.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-[5-chloro-3-(1,2-dihydroxyethyl)-2-ethoxy-4-methylphenyl]ethanone (0.64 g, 2.3 mmol) in tetrahydrofuran (18 mL) and water (11 mL) was added acetic acid (35 μL, 0.61 mmol) and sodium periodate (1.50 g, 7.04 mmol) at 0° C. After stirring for 30 min, the reaction mixture was diluted with water, and extracted with EtOAc. The combined extracts were washed with brine, dried over MgSO4, filtered and concentrated to give the desired product (0.58 g, 100%). LCMS calculated for C12H14ClO3 (M+H)+: m/z=241.1; Found: 241.1.

Workup

  1. extractionextracted with EtOAc
  2. washThe combined extracts were washed with brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-4533101485cf4f44bb23779194456b32
Source dataset
uspto-grants-2015_12
Patent number
US09199982B2

Reaction notes

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