Nitrogen → 2-Hydroxy-2-methyl-5-phenylpentane

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Reaction Steps

8 L of 3.0 M methylmagnesium chloride in ether was transferred to a 22 L 3-necked, round-bottomed flask using N2 pressure. This flask was equipped with argon flow inlet. The solution had been chilled to 0° in an ice-acetone bath and 1283 g (7.2 moles) quantity of methyl-4-phenylbutyrate was added under argon over 4 h maintaining the temperature between 0° C. and 11° C. The reaction mixture was stirred for 1H and an aliquot was withdrawn, quenched in water and extracted with ether. The ether extract was concentrated and the residual oil was assayed by NMR spectrum. This confirmed that no starting material remained. The reaction mixture was rechilled to 0° and 4 L of water was added over 3 to 4H. This caused vigorous gas evolution and slurrying during the initial stages of the addition and caused precipitation of a white solid. The reaction mixture was stirred for 1H following the water addition and the mixture was then filtered using Buchner funnel and the filtrate was separated. The aqueous phase was extracted with 2 L of ether-hexane mixture and the organic phases combined and concentrated to give 1200 g of yellow oil 94% yield.

Provenance & Evidence