BENZYL 3-HYDROXY-2,2-DIMETHYLPROPANOATE Chemical Properties

Boiling point:

117-118 °C(Press: 0.1 Torr)

Density 

1.100±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

pka

14.16±0.10(Predicted)

Appearance

Colorless to light yellow Liquid

BENZYL 3-HYDROXY-2,2-DIMETHYLPROPANOATE Usage And Synthesis

Synthesis

The general procedure for the synthesis of benzyl 2,2-dimethyl-3-hydroxypropionate from 2,2-dimethyl-3-hydroxypropionic acid and benzyl bromide was as follows: 2,2-dimethyl-3-hydroxypropionic acid (10.0 g) was dissolved in N,N-dimethylformamide (150 mL). Potassium bicarbonate (10.2 g) was added to this solution, followed by dropwise addition of benzyl bromide (10.7 mL). The reaction mixture was stirred at room temperature for 16 hours. Upon completion of the reaction, water (300 mL) was added to the mixture and extracted with a mixture of hexane and ethyl acetate (1:4, 200 mL x 2, by volume). The organic phases were combined and washed with saturated aqueous sodium chloride solution (200 mL) and subsequently dried over anhydrous magnesium sulfate. After filtration to remove the desiccant, the solvent was concentrated under reduced pressure to remove the solvent. The crude product obtained was purified by silica gel column chromatography (using medium-pressure preparative liquid chromatography, W-prep 2XY system manufactured by Yamazen Corporation; column: main column 4L, injection column 3L; eluent: hexane/ethyl acetate = 1:0 to 1:1, gradient time 15 min; fractionation mode GR) to afford the target product 2,2-dimethyl-3- benzyl hydroxypropionate (17.6 g, 100% yield). The product was confirmed by TLC (Rf value: 0.39, unfolding agent was n-hexane/ethyl acetate=3:1) and NMR (CDCl3, δ: 7.29-7.41 (m, 5H), 5.15 (s, 2H), 3.57 (d, J=6.3 Hz, 2H), 1.22 (s, 6H)).

References

[1] Patent: US2013/245074, 2013, A1. Location in patent: Paragraph 0391-0394
[2] Journal of the American Chemical Society, 2002, vol. 124, # 34, p. 9966 - 9967
[3] Patent: EP1544208, 2005, A1. Location in patent: Page/Page column 43
[4] Patent: EP1452526, 2004, A1. Location in patent: Page 55
[5] Tetrahedron, 2014, vol. 70, # 3, p. 590 - 596

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