Isopropylphenol

Choi, K., Sweet, L.I., Meier, P.G. and Kim, P.G. (2004) Aquatic toxicity of four alkylphenols (3-tert-butylphenol, 2-isopropylphenol, 3-isopropylphenol, and 4-iso-propylphenol) and their binary mixtures to microbes, invertebrates and fish, Environmental Toxicology 19, 45-50. 

Fig (22) 2-isopropylphenol (183) is converted to allylic alcohol (185). Its bromide derivative reacts with methyl acetoacetate. The resulting compound undergoes radical cyclization yields ketoester (186) whose vinyl triflate on reduction and carbonylation furnishes lactone (187). Diol (188) obtained from (187), is converted to monoepoxide (189) which on further epoxidation produces triptonide (148). Its conversion to triptolide (149) is accomplished by reduction. 

Monocyclic monoterpenes include the fully saturated menthol (5-methyl-2-isopropyl-cyclohexanol) (C6) (peppermint smell), the fully unsaturated analogue thymol (5-methyl-2-isopropylphenol) (G6) (smell of thyme) and the partially unsaturated a-terpinene (5,6-dihydro-4-isopropyltoluene) (G6) (lemon odour). Variants derive from different degrees of unsaturation and substitution and from different functional groups (e.g. alkyl, hydroxyl, aldehyde, peroxy and keto groups). 

C10H12 trans-(1 -methyl-1 -propenyl)benzene 768-00-3 249.65 14.589 2 20007 C10H14O 3-methyl-2-isopropylphenol 3228-01-1 342.15 19.325 2... 

C10H12 cis-1-methyl-4-(1-propenyl)benzene 2077-29-4 232.31 15.510 2 20011 C10H14O 5-methyl-2-isopropylphenol 89-83-8 322.85 21.300 1... 

A mixture of propan-2-one and phenol (5 1) passed through a ZnOj/AljOj catalyst held in a pyrex tube at 355" at 14 ml/min., followed by hydrogen at 100 ml/min. to give 2-isopropylphenol... 

The angular methyl octahydrophenanthrene depicted, a 2-isopropylphenol derivative, upon ozonation at -78°C in dichloromethane/methanol for 22 hours, followed by warming to ambient temperature and finally treatment with sodium borohydride in aqueous ethanol over 2 hours, has been reported to result in a decalenofuranone in 49% yield (ref.63), apparently by preferred cleavage at the di- and trisubstituted double bonds. 

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