Hydrochloric Acid → HCID 86603000, compound

Participants

Reaction Steps

A solution of (R,S)-1-[2-(1-Hydroxy-propyl)-phenyl]-propan-1-ol (4.0 g, 20.6 mmol) in pyridine (4.89 g, 61.7 mmol) was cooled with an ice-bath. Then phenyl phosphonic acid dichloride (4.03 g, 20.6 mmol) was added drop wise. The mixture was allowed to warm to ambient temperature, and stirred over night. To the mixture was then added HCl (ca. 20 ml 4N solution) and TBME (ca. 50 ml). The organic layer was separated, dried (sodium sulfate), and after removal of the solvent the product remained as a colourless oil. Yield: 5.88 g (90.3%). 1H/13C-NMR (CDCl3, HSQC/HMBC) δ/δ 1.05 (tr, J=7.4 Hz)/11.05 (CH3); 1.13 (tr, J=7.6 Hz)/10.48 (CH3); 2.05-2.21 (m)/27.82 (d, J=8.9 Hz), 30.61 (d, J=9.4 Hz) (2 CH2Me); 5.42 (ddd, J=4.7 Hz, J=5.8 Hz, J=8.5 Hz)/80.30 (d, J=7.6 Hz) (CHEt); 5.75 (ddd, J=3.8 Hz, J=5.3 Hz, J=7.4 Hz)/80.47 (d, J=7.3 Hz) (CHEt); 7.24/126.73 (Ar CH); 7.24/127.18 (Ar CH); 7.24/128.12 (Ar CH); 7.31/128.59 (Ar CH); 7.40/128.47 (d, J=15.2 Hz) (Ph meta-CH); 128.93 (d, J=192 Hz) (Ph ipso-C); 7.51/132.47 (d, J=3.1 Hz) (Ph para-CH); 7.73/131.74 (d, J=9.8 Hz) (Ph ortho-CH); 137.66, 138.92 (2 Ar ipso-C). 31P-NMR (CDCl3) δ 19.26.

Provenance & Evidence