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ChemicalBook CAS DataBase List Cyclobutanecarboxaldehyde
2987-17-9

Cyclobutanecarboxaldehyde synthesis

8synthesis methods
Cyclobutanecarboxaldehyde is generally prepared from cyclobutanecarboxylic acid and cyclobutanemethanol.
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Yield:2987-17-9 70.4%

Reaction Conditions:

Stage #1:cyclobutanemethanol with 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical;sodium hydrogencarbonate;potassium bromide in dichloromethane;water at -5; for 0.333333 h;
Stage #2: with sodium hypochlorite in dichloromethane;water at -5 - 0; for 0.5 h;
Stage #3: with potassium dihydrogenphosphate in dichloromethane;water at 20; for 0.5 h;

Steps:

1
Example 1; (Preparation of B); To a solution of compound A (cyclobutanemethanol) (100 g) in CH2Ck (1 L) was added a solution of 24% KBr in water (62.5 ml). To this mixture was added a solution of NaHCO3 in water (150 ml), and the mixture was cooled to - 50C. To this was added TEMPO reagent (1.8 g), and the mixture stirred for 20 min. Slowly 5% NaOCI (about 1900 ml) was charged to the mixture while maintaining the temperature between -50C to O0C. The mixture was then stirred for about 30 min. Then a solution of KH2PO4 in water (8.25%, 400 ml) was added and the mixture stirred for about an additional 30 min while warming to RT. The layers were then split and separated. The organic layer was dried with anhydrous MgSO4 and filtered. The dry organic layer was carefully distilled under partial vacuum (about 110 Torr) with a bath temperature about O0C to remove most of the solvent. The concentrate was further distilled at atmospheric pressure to obtain compound B (cyclobutanecarboxaldehyde) (70.6 g; 70.4%, 96% pure) as a colorless liquid: 1H NMR (400 MHz, CD3OD) 59.65 (1 H1 s), 3.05 (1 H1 m), 2.13 (2H, m), 2.03 (2H, m), 1.95 (1H, m), 1.80 (1 H1 m).

References:

SCHERING CORPORATION WO2008/82486, 2008, A2 Location in patent:Page/Page column 3; 11; 18; 20; 25; 38; 40; 43

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