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

HRID 1843779Notes

Reaction equation

HRID 1843779 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, 2 H), 4.10-4.11 (m, 1 H), 4.08-4.09 (m, 2 H), 4.01-4.02 (m, 1 H), 3.74-3.75 (m, 1 H), 2.58-2.59 (brs, 1 H), 2.45 (s, 3 H), 2.23 (s, 6 H), 2.05-2.10 (brs, 1 H); 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-60be9198c89b4e19937ed8d9ae01095d
Source dataset
uspto-grants-2015_02
Patent number
US08946268B2

Reaction notes

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