4'-Hydroxyacetophenone → 4'-(METHOXYMETHOXY)ACETOPHENONE

HRID 1244118Notes

Reaction equation

HRID 1244118 reaction equation
[CH3:1][O:2][CH2:3]Cl.[CH3:5][C:6]([C:8]1[CH:9]=[CH:10][C:11]([OH:14])=[CH:12][CH:13]=1)=[O:7].C(N(CC)CC)C>ClCCl>[CH3:1][O:2][CH2:3][O:14][C:11]1[CH:12]=[CH:13][C:8]([C:6](=[O:7])[CH3:5])=[CH:9][CH:10]=1

Participants

5

Reactant 3

HCID 74694'-HydroxyacetophenoneHCID 7864Chloromethyl Methyl EtherHCID 8471Triethylamine

Product 1

HCID 44249974'-(METHOXYMETHOXY)ACETOPHENONE

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Chloromethyl methyl ether (19.2 mL, 252 mmol) was added dropwise to a 0° C. solution of 4-hydroxyacetophenone (6.855 g, 50.35 mmol) and triethylamine (8.4 mL, 60.42 mmol) in dichloromethane (100 mL). The solution was then allowed to warm to rt overnight, quenched with MeOH (40 mL), filtered and the filtrate concentrated and purified by flash chromatography to give the title compound which was used as is in the next step.

Workup

  1. customquenched with MeOH (40 mL)
  2. filtrationfiltered
  3. concentrationthe filtrate concentrated
  4. custompurified by flash chromatography

Sources & evidence

ORD record
ord-2d80699d068e4b6ba1cbe4f644d0e01b
Source dataset
uspto-grants-2006_10
Patent number
US07119205B2

Reaction notes

Loading…