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Protection of phenyl glycinol using phthalic anhydride

SyntheticPage 609

Submitted: July 10, 2013, published: July 12, 2013

Authors

Nikola P. Chmel (N.Chmel@warwick.ac.uk)

Pratik Gurnani (pratik.gurnani@warwick.ac.uk)

A contribution from 

Reaction Scheme

Chemicals

(R)-phenylglycinol (Prepared in house, See page 275)
Phthalic anhydride (Aldrich)
Dichloromethane (Fischer Scientific)

Procedure

Solid (R)-phenylglycinol (2.0 g, 14.5 mmol) and phthalic anhydride (2.16 g, 14.5 mmol) were heated with stirring to 145°C for 4 h. The obtained yellow oil was dissolved in DCM (50 ml) and the solution was dried over anhydrous sodium sulphate. The solvent was then removed under reduced pressure and the product was used in the subsequent step without further purification. Yield 3.7 g (95%).

Author Comments

Worked smoothly and reproducibly

Data

1H NMR (400 MHz, 298 K, CDCl3) δH 7.83 – 7.74 (2H, m, Pht), 7.70 – 7.60 (2H, m, Pht), 7.49 (2H, d, 3JHH = 7.4 Hz, Ph), 7.41 – 7.23 (3H, m, Ph), 5.51 (1H, dd, 3JHH = 8.9 Hz, 3JHH = 5.0 Hz, CH), 4.76 – 4.66 (1H, m, CH2), 4.24 (1H, dd, 3JHH = 11.4 Hz, 4JHH = 4.9 Hz, CH2), 3.47 (1H, s, OH).

13C NMR (100 MHz, 298 K, CDCl3) δC 168.89 (C=O), 136.88, 134.08 (Pht), 131.72, 128.70, 128.13, 127.97 (Ph), 123.31 (Pht), 61.98 (CH2), 57.46 (CH).

MS (ESI+) m/z 290.1 ([M+Na]+)

IR (cm-1) ν 3457, 1772, 1700, 1611, 1585, 1495, 1467, 1388, 1358, 1332, 1288, 1266, 1185, 1172, 1120, 1065, 1040, 1013, 999, 962, 919, 877, 838, 793, 765, 719, 698.

Lead Reference

M. D. Chen, M. Z. He, X. Zhou, L. Q. Huang, Y. P. Ruan and P. Q. Huang, Tetrahedron, 2005, 61, 1335-1344 http://dx.doi.org/10.1016/j.tet.2004.10.109

Supplementary Information

Keywords

addition, alcohols, amines, phenyl glycinol, phthalic anhydride