Diethyl Ether → Benzeneacetic acid, 4-chloro-alpha-(1-methylethyl)-
Reaction equation
[CH:1]([CH:4]([C:8]1[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][CH:9]=1)[C:5](Cl)=[O:6])([CH3:3])[CH3:2].C(N(CC)CC)C.CC[O:24]CC>>[Cl:14][C:11]1[CH:12]=[CH:13][C:8]([CH:4]([CH:1]([CH3:3])[CH3:2])[C:5]([OH:24])=[O:6])=[CH:9][CH:10]=1Participants
Procedure
A solution was prepared by admixing 3.0 grams (0.014 mole) of 6-(phenoxy)picolinalcohol, 3.5 grams (0.015 mole) of 2-isopropyl-2-(4-chlorophenyl)acetic acid chloride 10 milliliters of triethylamine and 100 milliliters of dry ether. The reaction mixture was agitated at room temperature for 1 hour. The resulting reaction product mixture was successively washed with dilute hydrochloric acid, dilute sodium hydroxide, dried over anhydrous magnesium sulfate, filtered through silica gel and concentrated to give 5.3 grams of the desired 4-chloro-α-(1-methyl-ethyl)benzeneacetic acid:(6-phenoxy-2-pyridinyl)methyl ester. The product, a viscous yellow oil, had a refractive index of 1.5664 and the structure of the product was confirmed by NMR. Upon analysis, the product was found to have carbon, hydrogen and nitrogen contents of 68.83, 5.19 and 3.10 percent, respectively, as compared with the theoretical contents of 69.78, 5.60 and 3.54 percent, respectively, as calculated for the above named compounds (Compound No. 2).
Workup
- customA solution was prepared
- customThe resulting reaction product mixture
- washwas successively washed with dilute hydrochloric acid, dilute sodium hydroxide
- dry with materialdried over anhydrous magnesium sulfate
- filtrationfiltered through silica gel
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-56a84345b53c497287ffccaed01b2265
- Source dataset
- uspto-grants-1983_06
- Patent number
- US04390543
Reaction notes
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