alpha-Chloro-o-xylene → HCID 59186598, compound
Reaction equation
[CH3:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH2:4]Cl.[CH2:10]1[O:20][C:13]2([CH2:18][CH2:17][C:16](=[O:19])[CH2:15][CH2:14]2)[O:12][CH2:11]1>C1COCC1>[CH3:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH2:4][C:16]1([OH:19])[CH2:17][CH2:18][C:13]2([O:20][CH2:10][CH2:11][O:12]2)[CH2:14][CH2:15]1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
A solution of 2-methylbenzyl chloride (0.579 g, 4.12 mmol) in THF (20 mL) was treated with Mg (0.180 g, 7.50 mmol) and strirred at room temperature until all the Mg had dissolved. The mixture was cooled to 0° C., treated with a solution of 1,4-cyclohexanedione mono-ethylene ketal (0.579 g, 4.12 mmol) in THF (50 mL), warmed to room temperature, stirred overnight, quenched with saturated NH4Cl (100 mL), and extracted with ethyl acetate (3×100 mL). The combined extracts were washed with water and brine, dried (Na2SO4), filtered, and concentrated. The concentrate was purified by flash column chromatography on silica gel with 6:1 hexanes/ethyl acetate to provide the desired product (0.48 g, 44%) MS (ESI) m/e 262 (M+H)+.
Workup
- customstrirred at room temperature until all
- dissolutionhad dissolved
- temperaturewarmed to room temperature
- customquenched with saturated NH4Cl (100 mL)
- extractionextracted with ethyl acetate (3×100 mL)
- washThe combined extracts were washed with water and brine
- dry with materialdried (Na2SO4)
- filtrationfiltered
- concentrationconcentrated
- customThe concentrate was purified by flash column chromatography on silica gel with 6:1 hexanes/ethyl acetate
Sources & evidence
- ORD record
- ord-44680852f5a44dc38797a30ef8b5c9cd
- Source dataset
- uspto-grants-2009_09
- Patent number
- US07585858B2
Reaction notes
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