Ethylene Glycol → 2-(2,5-dimethylphenoxymethyl)phenyl 1,3-dioxolan-2-yl ketone O-methyloxime

HRID 1004384Notes

Reaction equation

HRID 1004384 reaction equation
C1C=CC=CC=1.[CH2:7]([OH:10])[CH2:8][OH:9].[CH3:11][C:12]1[CH:31]=[CH:30][C:29]([CH3:32])=[CH:28][C:13]=1[O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[C:22](=[N:25][O:26][CH3:27])[CH:23]=O>[Cl-].[Na+].O.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>[CH3:27][O:26][N:25]=[C:22]([CH:23]1[O:10][CH2:7][CH2:8][O:9]1)[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=1[CH2:15][O:14][C:13]1[CH:28]=[C:29]([CH3:32])[CH:30]=[CH:31][C:12]=1[CH3:11]

Participants

6

Reactant 3

HCID 174Ethylene GlycolHCID 241BenzeneHCID 538610512-(2,5-Dimethylphenoxymethyl)-alpha-methoxyiminophenylacetaldehyde

Product 1

HCID 540722312-(2,5-dimethylphenoxymethyl)phenyl 1,3-dioxolan-2-yl ketone O-methyloximeYield 87.9%

Reagents, catalysts & solvents 2

HCID 521998p-Toluenesulfonic acid monohydrateCatalystHCID 57417360Sodium chloride; waterSolvent

Procedure

Benzene (4 ml), ethylene glycol (0.12 g, 2.0 mmol) and p-toluenesulfonic acid monohydrate (0.01 g, 0.05 mmol) were added to 2-(2,5-dimethylphenoxymethyl)-α-methoxyiminophenylacetaldehyde (0.3 g, 1.0 mmol), and the mixture was subjected to azeotropic dehydration for 2 hours. After completion of the reaction, half-saturated brine (100 ml) was added, and the mixture was extracted with dichloromethane (50 ml) twice. The extracts were dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel chromatography (ethyl acetate/n-hexane) to give 2-(2,5-dimethylphenoxymethyl)phenyl 1,3-dioxolan-2-yl ketone O-methyloxime (0.30 g, yield 87.9%) as colorless crystals. mp 136-137° C.

Workup

  1. additionwas added
  2. extractionthe mixture was extracted with dichloromethane (50 ml) twice
  3. dry with materialThe extracts were dried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel chromatography (ethyl acetate/n-hexane)

Sources & evidence

ORD record
ord-ce0b1ef346e1469d98d98d56fb2dfb39
Source dataset
uspto-grants-2000_04
Patent number
US06048885

Reaction notes

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