4-isopropyl-m-cresol synthesis

12synthesis methods

Product Name:4-isopropyl-m-cresol
CAS Number:1740-97-2
Molecular formula:C10H14O
Molecular Weight:150.22

68591-07-1
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1740-97-2
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Yield:1740-97-2 84%

Reaction Conditions:

with 5%-palladium/activated carbon;hydrogen;toluene-4-sulfonic acid in methanol at 20; under 18751.9 Torr; for 12 h;Autoclave;

Steps:

1.b Preparation of 2-methyl 4 isopropyl phenol

In a s/s 150 mL autoclave a solution of the 2-hydroxy-5-isopropylbenzaldehyde (29.5 g, 179 mmol) in methanol (50 ml) containing pTSA (100 mg) and palladized charcoal (5 %,1.0 g) was evacuated under vacuum and purged with hydrogen gas 5 times then stuffed under an atmosphere of hydrogen gas (25 bar) for 12 hours at ambient temperature. The suspension was filtered and washed with MTBE (2 x 100 mL) then the filtrate washed with NaHCO3 solution dried and the solvents removed in vacuo to yield the crude phenol, 30 g. Further purification by bulb to bulb (Kugelrohr) distillation temp 120°C vacuum1 mbar gave the pure phenol, 26.5 g (84 %).‘H NMR (400 MHz, CDC13): ‘Y 1.20 (d, J 6.7, 6H), 2.22 (s, 3H), 2.80 (m7, J 6.9, 1H), 4.93 (bs, 1H), 6.68 (d, J7.9, 1H), 6.91 (dd, J7.9, 1.4, 1H), 6.97 (d, J 1.4, 1H) ppm;‘3C NMR (100 MHz, CDC13): ‘Y 15.9 (q), 24.2 (q), 33.3 (d), 114.7 (d), 123.5 (s), 124.8 (d), 129.0 (d), 141.2 (s), 151.6 (s) ppm.

References:

WO2018/167200,2018,A1 Location in patent:Page/Page column 14; 15

33426-60-7 Synthesis