2-methyl-1-phenoxypropan-2-ol synthesis

7synthesis methods

Product Name:2-methyl-1-phenoxypropan-2-ol
CAS Number:13524-74-8
Molecular formula:C10H14O2
Molecular Weight:166.22

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Yield:13524-74-8 2.1 g (91% recovery)

Reaction Conditions:

with methylmagnesium bromide in diethyl ether;

Steps:

26 1,1-Dimethyl-2-phenoxyethanol

PREPARATION 26 1,1-Dimethyl-2-phenoxyethanol To a stirred solution of 24.2 g (0.16 mole) of phenoxy-2-propanone (Eastman) in 150 mL of dry ethyl ether was added 56 ml (0.17 mole) of methylmagnesium bromide (3.0M solution in ethyl ether, Aldrich) and the reaction mixture was stirred at ambient temperature under a nitrogen atmosphere for 4 hr. The reaction mixture was treated with 100 ml of saturated ammonium chloride solution and vigorously stirred for 1 hr. The layers were separated and the organic layer was washed twice with 200 ml portions of water, dried (magnesium sulfate) and the solvent evaporated under reduced pressure to yield 24.3 g (91%) of a vicous oil. A 2.3 g sample of the oil was purified by high pressure liquid chromatography (Waters Associates Prep LC/System 500 A, PrepPak 500 silica, ethyl acetate-hexanes, 1:20, flow rate 150 ml/min). The desired fractions were combined and the solvents evaporated under reduced pressure to yield 2.1 g (91% recovery) of the title compound as a colorless liquid. Analysis: Calculated for C₁₀ H₁₄ O₂: C, 72.26; H, 8.49. Found: C, 72.08; H, 8.46.

References:

US5192785,1993,A