3-Chloro-1,2-propanediol → HCID 58442471, compound

HRID 1480701Notes

Reaction equation

HRID 1480701 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.Cl[CH2:14][CH:15]([OH:18])[CH2:16][OH:17]>[OH-].[Na+].O>[OH:18][CH:15]([CH2:16][OH:17])[CH2:14][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 72903-Chloro-1,2-propanediolHCID 40573701-(4-Hydroxy-2,6-dimethylphenyl)ethanone

Product 1

HCID 58442471HCID 58442471, compoundYield 57.4%

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 (2.00 g, 12.2 mmol, 1.0 equiv) and 3-chloropropane-1,2-diol (1.02 mL, 12.2 mmol, 1.0 equiv) in 50% aqueous NaOH solution (20.0 mL) was heated at 140° C. for 16 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-(2,3-dihydroxypropoxy)-2,6-dimethylphenyl)ethanone (1.66 g, 7.0 mmol) as yellow oil in 57% yield: 1H NMR (CDCl3, 500 MHz) δ 6.57 (s, 2H), 4.10-4.11 (m, 1H), 4.08-4.09 (m, 2H), 4.01-4.02 (m, 1H), 3.74-3.75 (m, 1H), 2.58-2.59 (brs, 1H), 2.45 (s, 3H), 2.23 (s, 6H), 2.05-2.10 (brs, 1H); ESI-MS: m/z 239.9 (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-13414fd84016466bac1873f2cd6f4bfa
Source dataset
uspto-grants-2016_08
Patent number
US09409902B2

Reaction notes

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