Chloromethyl Methyl Ether → HCID 57742154, compound

HRID 660320Notes

Reaction equation

HRID 660320 reaction equation
[CH2:1]([O:3][C:4](=[O:13])[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([OH:12])[CH:7]=1)[CH3:2].[H-].[Na+].[CH2:16](Cl)[O:17][CH3:18]>C1COCC1.O>[CH2:1]([O:3][C:4](=[O:13])[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([O:12][CH2:16][O:17][CH3:18])[CH:7]=1)[CH3:2]

Participants

6

Reactant 3

HCID 7864Chloromethyl Methyl EtherHCID 24758Sodium hydrideHCID 572437Ethyl (3-Hydroxyphenyl)acetate

Product 1

HCID 57742154HCID 57742154, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (3-Hydroxy-phenyl)-acetic acid ethyl ester (27.6 g) in THF was added NaH (7.35 g), MOM-Cl (14.8 g) slowly at 0°. After stirred for 14 h at the same temperature, the reaction mixture was warmed to room temperature. The resulting mixture was diluted with water and extracted with EtOAc. The combined organic layer was dried over magnesium sulfate, filtered and concentrated in vacuo. The resulting residue was chromatographed on silica gel (n-Hex:EtOAc=15:1 to 10:1) to afford the product as colorless oil. (31.2 g, 90.9%)

Workup

  1. extractionextracted with EtOAc
  2. dry with materialThe combined organic layer was dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe resulting residue was chromatographed on silica gel (n-Hex:EtOAc=15:1 to 10:1)

Sources & evidence

ORD record
ord-829b6dd1c705454b8688e0ae3af37fa8
Source dataset
uspto-grants-2011_12
Patent number
US08084484B2

Reaction notes

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