Sodium Chloride → trans-3,3-Dimethyl-2-acetyl-cyclopropanecarbaldehyde
Reaction equation
C(O)(C)(C)C.[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:12][C:13]1([CH3:22])[C@@H:15]([C:16](Cl)=[O:17])[C@@H:14]1[C:19](=[O:21])[CH3:20].[Cl-].[Na+]>O1CCCC1.CCOCC>[CH3:12][C:13]1([CH3:22])[C@@H:15]([CH:16]=[O:17])[C@@H:14]1[C:19](=[O:21])[CH3:20]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
36.6 g (0.495 mol) of tert.-butanol were added dropwise, at 20°-30° C., to a mixture of 6.3 g (0.165 mol) of lithium aluminum hydride and 100 ml of tetrahydrofuran in the course of 1 hour. The mixture was subsequently stirred for 2 hours at room temperature and was then added dropwise, at -50° to -60° C., to a solution of 26.1 g (0.15 mol) of trans-3,3-dimethyl-2-acetyl-cyclopropanecarboxylic acid chloride in 75 ml of tetrahydrofuran. When the addition was complete, the mixture was subsequently stirred for 1 hour, without cooling, and poured onto a mixture of 30 ml of concentrated sodium chloride and 300 g of ice, and extraction was carried out by shaking with twice 400 ml of ether. The organic phases were washed first with 50 ml of saturated sodium bicarbonate solution and then with 100 ml of water, dried over sodium sulphate and evaporated in vacuo. 12.7 g (62% of theory) of trans-3,3-dimethyl-2-acetyl-cyclopropanecarboxaldehyde were obtained, by vacuum distillation of the residue, in the form of a colorless oil having a boiling point of 80° -86° C./10 mbar.
Workup
- additionWhen the addition
- stirringthe mixture was subsequently stirred for 1 hour
- temperaturewithout cooling
- washThe organic phases were washed first with 50 ml of saturated sodium bicarbonate solution
- dry with materialwith 100 ml of water, dried over sodium sulphate
- customevaporated in vacuo
Sources & evidence
- ORD record
- ord-564bb754613e4cbea3b55c95dea15c7a
- Source dataset
- uspto-grants-1982_08
- Patent number
- US04342704
Reaction notes
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