ChemInform Abstract: Reductive Oxidation of Acid Chlorides to Aldehydes with Lithium Aluminum Hydride and Pyridinium Chlorochromate or Pyridinium Dichromate.

ChemInform ◽  
2000 ◽  
Vol 31 (44) ◽  
pp. no-no
Author(s):  
Jin Soon Cha ◽  
Joong Hyun Chun
Keyword(s):  
Lithium Aluminum Hydride ◽  
Aluminum Hydride ◽  
Lithium Aluminum ◽  
Pyridinium Chlorochromate ◽  
Acid Chlorides

The Preparation of Specifically Deuterated trans- Cinnamyl Alcohol and trans- Cinnamic Acid

1973 ◽  
Vol 51 (13) ◽  
pp. 2102-2104 ◽  
Author(s):  
Donald G. Lee ◽  
James R. Brownridge
Keyword(s):  
Cinnamic Acid ◽  
Triple Bond ◽  
Lithium Aluminum Hydride ◽  
Aluminum Hydride ◽  
Lithium Aluminum ◽  
Cinnamyl Alcohol ◽  
Partial Reduction ◽  
Work Up

The reduction of ethyl phenylpropiolate by lithium aluminum hydride results in partial reduction of the triple bond to give trans-cinnamyl alcohol. If ethyl phenylpropiolate is reduced by LiAlD4 followed by work-up with acetone and H2O the product is the specifically labeled compound, trans-3-phenyl-2-propen-1-ol-1,1,2-d3. If the ester is reduced with LiAlH4 followed by work-up with acetone-d6 and D2O the product is trans-3-phenyl-2-propen-1-ol-O,3-d2. Oxidation of these two products by sodium ruthenate leads to formation of trans-cinnamic acid-α-d and trans-cinnamic acid-β-d, respectively.

Sign in / Sign up

Export Citation Format

Share Document