2,6-Dimethylphenol → HCID 53817232, compound
Reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[C:5](Cl)(=[O:8])[CH2:6][CH3:7].[CH3:10][C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([CH3:17])[C:12]=1[OH:18]>C(Cl)Cl>[C:5]([O:18][C:12]1[C:13]([CH3:17])=[CH:14][C:15]([C:5](=[O:8])[CH2:6][CH3:7])=[CH:16][C:11]=1[CH3:10])(=[O:8])[CH2:6][CH3:7]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
To a mixture of aluminum chloride (32.0 g, 24 mmol) in methylene chloride (100 mL) was added propionyl chloride (3.56 mL, 40.95 mmol) all at once followed by 2,6-dimethylphenol (5.0 g, 40.93 mmol in 25 mL of methylene chloride) over 5 min. After stirring 1 h at ambient temperature a second equivalent of propionyl chloride was added (3.56 mL). The reaction was stirred 2 h more and then carefully quenched with water. The mixture was extracted with ether (3x) and the combined organic phase was washed with aqueous bicarbonate and brine; then it was dried over magnesium sulfate and concentrated to give 8.18 g (85%) of 2,6-dimethyl-4-propionylphenyl propionate as a waxy tan solid which had: NMR δ7.68 (s, 2 H), 2.95 (q, J=7.3 Hz, 2 H), 2.65 (q, J=7.5 Hz, 2 H), 2.19 (s, 6 H), 1.32 (t, J=7.6 Hz, 3 H), 1.20 (t, J=7.3 Hz, 3 H). This product also contained some minor impurities in the NMR spectrum but was found suitable for use without further purification.
Workup
- additionwas added (3.56 mL)
- customcarefully quenched with water
- extractionThe mixture was extracted with ether (3x)
- washthe combined organic phase was washed with aqueous bicarbonate and brine
- dry with materialthen it was dried over magnesium sulfate
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-e959aca5e2ad47e0ab5ea6449d2f8ade
- Source dataset
- uspto-grants-2001_07
- Patent number
- US06258827B1
Reaction notes
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