2-Chloroethyl methyl ether → HCID 58442521, compound

HRID 1465645Notes

Reaction equation

HRID 1465645 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][O:16][CH3:17]>[OH-].[Na+].O>[CH3:17][O: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 123162-Chloroethyl methyl etherHCID 40573701-(4-Hydroxy-2,6-dimethylphenyl)ethanone

Product 1

HCID 58442521HCID 58442521, compoundYield 64%

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 1-chloro-2-methoxyethane (0.28 mL, 3.1 mmol, 1.0 equiv) in 50% aqueous NaOH solution (5.0 mL) was heated 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 with MgSO4, and concentrated under reduced pressure to give 1-(4-(2-methoxyethoxy)-2,6-dimethylphenyl)ethanone (430.9 mg, 1.9 mmol) as yellow oil in 64% yield: 1H NMR (CDCl3, 500 MHz) δ 6.58 (s, 2 H), 4.09-4.10 (m, 2 H), 3.72-3.74 (m, 2 H), 3.44 (s, 3 H), 2.45 (s, 3 H), 2.23 (s, 6 H); ESI-MS: m/z 223.6 (M+H)+.

Workup

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

Sources & evidence

ORD record
ord-c70410b23fe5403da7fb7d3a9fe2feca
Source dataset
uspto-grants-2015_04
Patent number
US08999983B2

Reaction notes

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