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

HRID 481472Notes

Reaction equation

[CH:1]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH:10]([CH3:12])[CH3:11])[C:5]=1[OH:13])([CH3:3])[CH3:2].C1N2CN3CN(C2)CN1C3.CCCCCC.FC(F)(F)[C:32](O)=[O:33]>>[CH:10]([C:6]1[CH:7]=[C:8]([CH:9]=[C:4]([CH:1]([CH3:3])[CH3:2])[C:5]=1[OH:13])[CH:32]=[O:33])([CH3:12])[CH3:11]

Participants

Reactant 4

HCID 4101Hexamethylenetetramine

HCID 4943Propofol

HCID 6422Trifluoroacetic acid

HCID 8058Hexane

Product 1

HCID 827124-Hydroxy-3,5-bis(isopropyl)benzaldehydeYield 26%

Procedure

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.

Sources & evidence

ORD record: ord-b7f51b40ba65469a88d14e33928d8ba7
Source dataset: uspto-grants-1998_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05789427

Reaction notes

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