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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 30, 2000 - Issue 22
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Original Articles

A Convenient Synthesis of 2-Phenylglycerol

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Pages 4027-4038 | Received 30 Jan 2000, Published online: 04 Dec 2007

References

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  • The preparation and biological assessment of our final compounds, along with our theoretical and synthetic studies associated with formation of the oxetane will be published elsewhere.
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  • The dollar cost per gram for various starting materials and Scheme 1 intermediates based upon approximate 100 gram lots as available from Aldrich Chemical Co. (1998--1999 catalogue) are as follows: Scheme 1 acetophenone (2) = 0.05, α-hydroxyacetophenone = 2.70 and 2-phenyl-1,2-propanediol = 2.90; Scheme 2 α-methylstyrene (3) = 0.15; Scheme 3 α-bromoacetophenone = 0.42; Scheme 4 1,3-dihydroxyacetone Dimer = 0.22.
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  • Yorozu , K. , Takai , T. , Yamada , T. and Mukaiyama , T. 1994 . Bull Chem. Soc. Jpn. , 67 : 2195 melting point = 87 to 89°C.
  • Aldrich Chem. Co. Acros Organics/Fisher Scientific . melting point = 86 to 89°C. melting point = 86 to 88°C.
  • Eliel , E. L. and Freeman , J. P. 1958 . J. Am. Chem. Soc. , 74 923 melting point = 44 to 45°C.
  • Aldrich Chem. Co. mp = 44 to 45°C.
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  • The propensity for acylated glycerols to readily undergo transesterifications is exemplified by diacetin (diacetylglycerol) which is sold by Aldrich Chemical Co. as a mixture of the 1,2-1,3- and 1,2,3-di/triacetylglycerols.
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  • In addition to the higher melting point observed for the hydrated crystals, x-ray diffraction studies have confirmed that 2 molecules of H2O pack between four molecules of 2-phenylglycerol indicating that this water is an inherent component of the unit cell within this particular crystalline species. Our x-ray results will be published elsewhere as part of preliminary theoretical studies pertaining to ring closures within variously substituted glycerols.

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