1-Methoxy-2-propanol → 2',6'-Dimethyl-N-(2-Methoxy-1-Methylethoxymethyl) 2-Chloroacetanilide

HRID 466343Notes

Reaction equation

HRID 466343 reaction equation
[CH3:1][C:2]1[CH:14]=[CH:13][CH:12]=[C:11]([CH3:15])[C:3]=1[N:4]([CH2:9]Cl)[C:5](=[O:8])[CH2:6][Cl:7].[CH3:16][O:17][CH2:18][CH:19]([CH3:21])[OH:20]>C(Cl)CCl>[CH3:1][C:2]1[CH:14]=[CH:13][CH:12]=[C:11]([CH3:15])[C:3]=1[N:4]([CH2:9][O:20][CH:19]([CH3:21])[CH2:18][O:17][CH3:16])[C:5](=[O:8])[CH2:6][Cl:7]

Participants

4

Reactant 2

HCID 79001-Methoxy-2-propanolHCID 130698822-Chloro-N-(chloromethyl)-N-(2,6-dimethylphenyl)acetamide

Product 1

HCID 538049682',6'-Dimethyl-N-(2-Methoxy-1-Methylethoxymethyl) 2-ChloroacetanilideYield 99.1%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

About 12.3 g (0.050 mole) of 2',6'-dimethyl-N-(chloromethyl) 2-chloroacetanilide dissolved in twenty (20) ml of ethylene dichloride was added to 22.5 g (0.25 mole) of 2-methoxy-1-methyl ethanol. The solution was allowed to stand one hour at room temperature. Excess alcohol and HCl was removed under vacuum on a rotary evaporator. The residual oil was treated with an additional 22.5 g fresh alcohol for 30 minutes at 60° C. Excess alcohol and HCl was removed as before at 65° C./1 mm Hg. The light yellow oily residue weighed 14.86 g (99.1% yield). Refractive index of the oil, n26D 1.5263. Proton NMR was consistent with structure.

Workup

  1. customExcess alcohol and HCl was removed under vacuum on a rotary evaporator
  2. additionThe residual oil was treated with an additional 22.5 g fresh alcohol for 30 minutes at 60° C
  3. customExcess alcohol and HCl was removed as before at 65° C./1 mm Hg

Sources & evidence

ORD record
ord-0eb9537c996a4f38abfb6431391683cf
Source dataset
uspto-grants-1992_10
Patent number
US05155272

Reaction notes

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