Propylene Oxide → HCID 58442539, compound

HRID 1480700Notes

Reaction equation

HRID 1480700 reaction equation
[OH:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([C:9](=[O:11])[CH3:10])=[C:4]([CH3:12])[CH:3]=1.[CH3:13][CH:14]1[CH2:16][O:15]1>[OH-].[Na+].O>[OH:15][CH:14]([CH3:16])[CH2:13][O:1][C:2]1[CH:3]=[C:4]([CH3:12])[C:5]([C:9](=[O:11])[CH3:10])=[C:6]([CH3:8])[CH:7]=1

Participants

5

Reactant 2

HCID 6378Propylene OxideHCID 40573701-(4-Hydroxy-2,6-dimethylphenyl)ethanone

Product 1

HCID 58442539HCID 58442539, compoundYield 67.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 14798Sodium HydroxideSolvent

Conditions

Temperature
140 °C

Procedure

A pressure glass vessel charged with 1-(4-hydroxy-2,6-dimethylphenyl)ethanone (500 mg, 3.1 mmol, 1.0 equiv) and 2-methyloxirane (0.22 mL, 3.1 mmol, 1.0 equiv) in 50% aqueous NaOH solution (5.0 mL) was stirred at 140° C. for 4.0 h. The mixture was diluted with H2O (20 mL) and extracted with EtOAc. The organic layer was collected, dried over MgSO4(s), and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (30% EtOAc in hexanes as eluant) to provide 1-(4-(2-hydroxypropoxy)-2,6-dimethylphenyl)ethanone (445.9 mg, 2.1 mmol) as yellow oil in 66% yield: 1H NMR (CDCl3, 500 MHz) δ 6.57 (s, 2H), 4.10-4.20 (brs, 1H), 3.90-3.93 (m, 2H), 3.75-3.79 (m, 1H), 2.45 (s, 3H), 2.23 (s, 6H), 1.25-1.28 (m, 3H); ESI-MS: m/z 223.4 (M+H)+.

Workup

  1. extractionextracted with EtOAc
  2. customThe organic layer was collected
  3. dry with materialdried over MgSO4(s)
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by column chromatography on silica gel (30% EtOAc in hexanes as eluant)

Sources & evidence

ORD record
ord-5cbc2e477de84d248e1378a36eb75c49
Source dataset
uspto-grants-2016_08
Patent number
US09409902B2

Reaction notes

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