All Notebooks | Help | Support | About
3rd October 2016 @ 23:20

This is the first step in the synthesis of 2-phenyl-2-tetrahydro-2H-pyran-2-yl)oxy)ethan-1-ol, needed to continue the next step of primary synthesis outlined in issue #430.

Procedure based off AEW 173-1.

(Started 9/21)

 

compound

MW (g/mol)

mol (mmol) g           density (g/mL) volume (mL) equivalents
DL-mandelic acid 152.15 32.9 5.010     1

p-TsOH

172.2 0.33 0.061     0.01
MeOH         66  
MRLS 5-1 166.18 32.9       1

Procedure:

Weighed out DL-mandelic acid (5.010 g, 33 mmol) into round bottom. Added 0.0610 g of p-TsOH and 66 mL of MeOH and stirred. Refluxed under Argon for 12 hours. 

(came in after ~6 hours to find the variac had turned off. Started the reflux again.)

TLC showed most of starting material was consumed. 

Removed solvent under reduced pressure and took NMR (96.6% yield, 31.8 mmol, 5.2874 g).

Used product as starting material for MRLS 6-1.

Attached Files
MRLS 5-1 better.JPG
MRLS 5-1 carbon spectrum.pdf
GCMS
1 H