Benzyloxyacetone

Uses

Benzyloxyacetone (1-Benzyloxy-2-propanone) may be used in the synthesis of:

• 7-benzyloxy-6-methyl-5-hepten-1-yne
• (Z)-2-methylhept-2-en-6-yn-1-o1
• (S)-(+)-1,2-propanediol, 1-benzyl ether

General Description

Benzyloxyacetone (α-Benzyloxyacetone) is an α-substituted acetone. It undergoes direct aldol reaction with 4-nitrobenzaldehyde in the presence of (S)-BINAM-L-prolinamide/benzoic acid to form predominantly the syn-diasteroisomer.

Synthesis

14593-43-2

22539-93-1

To a stirred mixed solution of allyl benzyl ether (0.4 mmol) in acetonitrile (3.5 mL) and water (0.5 mL) was added palladium dichloride (PdCl2, 3.6 mg, 0.02 mmol, 5 mol%) and chromium trioxide (CrO3, 20 mg, 0.6 mmol, 0.5 eq.), in that order, at room temperature. The reaction mixture was heated to 60°C and stirred in a closed flask for the indicated time (refer to Table 5-7). Upon completion of the reaction, the mixture was filtered through a small silica gel pad and washed with ethyl acetate (EtOAc), followed by concentration of the filtrate. In some cases, the residue is almost pure in the residue and no further purification is required. In the remaining cases, the residue needs to be purified by silica gel column chromatography using petroleum ether/ethyl acetate (EtOAc) as eluent to finally obtain benzyloxyacetone.

References

[1] Tetrahedron, 2014, vol. 70, # 32, p. 4760 - 4767
[2] Journal of Organic Chemistry, 2016, vol. 81, # 5, p. 2113 - 2121
[3] Journal of Organic Chemistry, 2014, vol. 79, # 12, p. 5787 - 5793
[4] Tetrahedron Letters, 2013, vol. 54, # 19, p. 2293 - 2295
[5] Tetrahedron Letters, 2009, vol. 50, # 24, p. 2893 - 2894