1-Chloro-3-methoxypropane → HCID 58442478, compound

HRID 1843783Notes

Reaction equation

HRID 1843783 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][CH2:15][CH2:16][O:17][CH3:18]>[OH-].[Na+].O>[CH3:18][O:17][CH2:16][CH2:15][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 1189271-Chloro-3-methoxypropaneHCID 40573701-(4-Hydroxy-2,6-dimethylphenyl)ethanone

Product 1

HCID 58442478HCID 58442478, compoundYield 86%

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 (800 mg, 4.9 mmol, 1.0 equiv) and 1-chloro-3-methoxypropane (528.97 mg, 4.9 mmol, 1.0 equiv) in 50% aqueous NaOH solution (10.0 mL) was stirred at 140° C. for 16 h. The residue was diluted with H2O (20 mL) and extracted with EtOAc (3×30 mL). The organic layer was separated, dried over MgSO4(s), and concentrated under reduced pressure to give 1-(4-(3-methoxypropoxy)-2,6-dimethylphenyl)ethanone (987.8 mg, 4.2 mmol) as yellow oil in 86% yield: 1H NMR (DMSO-d6, 500 MHz) δ 6.56 (s, 2 H), 4.02-4.04 (m, 2 H), 3.53-3.55 (m, 2 H), 3.36 (s, 3 H), 2.45 (s, 3 H), 2.23 (s, 6 H), 2.02-2.04 (m, 3H); ESI-MS: m/z 237.7 (M+H)+.

Workup

  1. extractionextracted with EtOAc (3×30 mL)
  2. customThe organic layer was separated
  3. dry with materialdried over MgSO4(s)
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-a0026f3d1f09469caf4964391dee7ce4
Source dataset
uspto-grants-2015_02
Patent number
US08946268B2

Reaction notes

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