ChemicalBook CAS DataBase List 2-Methylbenzyl alcohol

2-Methylbenzyl alcohol synthesis

14synthesis methods

Product Name:2-Methylbenzyl alcohol
CAS Number:89-95-2
Molecular formula:C8H10O
Molecular Weight:122.16

50-00-0 Synthesis

50-00-0
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$10.00/25g

16419-60-6 Synthesis

16419-60-6
380 suppliers
$9.00/1g

89-95-2
207 suppliers
$22.00/10g

Yield:89-95-2 81%

Reaction Conditions:

with bis(η3-allyl-μ-chloropalladium(II));1-(2-bromophenyl)-3-(2,6-diisopropylphenyl)-4,5-dihydroimidazolinium chloride in tetrahydrofuran;water at 100; for 2 h;Inert atmosphere;Sealed tube;

Steps:

General procedure for the palladium catalyzed hydroxylmethylationof arylboronic acid 3b and ieq using aqueousformaldehyde 2n
General procedure: [PdCl(η³-allyl)]₂ (0.00125-0.005 mmol), imidazolinium salt 1a (0.0025-0.01 mmol), arylboronic acid (0.50 mmol) and an inorganic base (2.0 mmol) were charged in a 10 mL test tube sealed with a rubber septum. The test tube was evacuated and backfilled with argon. This sequence was repeated five times. Then solvent (0.5 mL) and 37 wt % formaldehyde in H₂O (102 mg, formaldehyde 1.25 mmol) were added via the rubber septum with syringe. In anargon flow, the rubber septum was replaced with a Teflon liners crew cap. The test tube was placed in an oil bath preheated at 100 C. The reaction mixture was stirred for 2 h and was cooled to room temperature. Then, operation of (i) or (ii) was performed. (i)The obtained crude was purified by passing it through a silica gel column with a hexane/ethyl acetate eluent (Table 4 entry 2 and Table 5 entries 8-16). (ii) Diphenylmethane (84.1 mg, 0.50 mmol) as an internal standard was added and then an aliquot of the organic layer of the reaction mixture was subjected to the quantitative analysis by 1H NMR (Table 4).

References:

Yamamoto, Tetsuya;Furusawa, Takuma;Zhumagazin, Azamat;Yamakawa, Tetsu;Oe, Yohei;Ohta, Tetsuo [Tetrahedron,2014,vol. 71,# 1,p. 19 - 26]

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