
TY  - JOUR
A1  - Collins, DJ 
A1  - Jacobs, HA 
T1  - Synthesis of 3-(4&#8242;-Methoxyphenyl)-2,2,4,4-Tetramethylpentane and Some Cyclic Analogs
JF  - Australian Journal of Chemistry
JO  - Aust. J. Chem.
Y1  - 1986
VL  - 39
IS  - 12
SP  - 2095
EP  - 2110
KW  - 
UR  - https://doi.org/10.1071/CH9862095 
N2  - Reaction of 1-methoxy-2-methyl-1-trimethylsilyloxyprop-1-ene (8) with 1-acetoxy-1-(4&#8242;-methoxyphenyl)-2,2-dimethylpropane (7b) in the presence of zinc iodide gave 84% of methyl 3-(4&#8242;methoxyphenyl)-2,2,4,4- tetramethylpentanoate (9a), which was reduced with lithium aluminium hydride to 3-(4&#8242;-methoxyphenyl)-2,2,4,4-tetramethylpentan-1-ol(12a). Hydride reduction of the derived tosylate (12b) afforded 3-(4&#8242;-methoxyphenyl )-2,2,4,4-tetramethylpentane (5b) which upon demethylation yielded the corresponding phenol (10a). In an analogous manner, 1-acetoxy-1-(4&#8242;-methoxyphenyl)-2-methylpropane (7d) was converted into 3- (4&#8242;-hydroxyphenyl)-2,2,4-trimethylpentane (10b). By a similar reaction sequence, 6-methoxy-2,2-dimethyl-3,4- dihydronaphthalen-1(2H)-one (14) was transformed into 6-hydroxy-2,2- dimethyl-1-(1&#8242;,1&#8242;-dimethylethyl)-1,2,3,4-tetrahydronaphthalene (16b). Hydrolysis of the ester (9a) and cyclization of the resulting carboxylic acid (19) by treatment with methanesulfonic acid at 20&#176; for 18 h afforded 3-(1&#8242;, 1&#8242;-dimethylethyl)-6-methoxy-2,2-dimethyl-2,3-dihydro-1H-inden-1-one (20). Clemmensen reduction of this followed by demethylation yielded 1-(1&#8242;,1&#8242;-dimethylethyl)-2,2-dimethyl-2,3-dihydro-1H-inden-5-ol (21b). Attempts to oxidize the phenols (10a), (10b), (16b) and (21b) to the corresponding quinone  methides by conventional methods failed. 
ER  -

