Hexamethylenetetramine → 4-Hydroxy-3,5-bis(isopropyl)benzaldehyde

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Reaction Steps

18 g of 2,6-di isopropyl phenol and 1.8 g HMTA (hexamethylene tetraamine) in 60 ml TFA (trifluoro acetic acid) was refluxed 3.5 hours. Workup, chromatography on silica gel (CH2Cl2) and trituration with hexane gave 5.3 g, 26% yield, white solid, mp-103° C. (3,5,-di-iso-propyl 4 hydroxybenzaldehyde). NMR CDCl3 δ 9.87 (1H,S,CHO), 7.63 (2H,S), 3.19 (2H,septet,J=7.7 Hz), 1.30 (12H,d,J=7.7 Hz). 0.4 g of 3,5,-diisopropyl-4-hydroxy benzaldehyde), 0.15 g of malononitrile and 3 drops piperidine in 30 ml ethanol were refluxed 3.5 hours. Workup and trituration with hexane gave 0.28 g, 56% yield, yellow solid, mp-150° C. NMR CDCl3 δ 7.69 (2H,S), 7.65 (1H,S,vinyl), 3.16 (2H,septet,J=7.0 Hz), 1.29 (12H,d,J=7.0 Hz). MS-254 (M+,59), 239 (M-CH3,95), 197 (M-2CN3 -HCN, 100%), 149 (25), m/e.

Provenance & Evidence