ChemicalBook CAS DataBase List 3-Methylphenethyl alcohol

3-Methylphenethyl alcohol synthesis

11synthesis methods

Product Name:3-Methylphenethyl alcohol
CAS Number:1875-89-4
Molecular formula:C9H12O
Molecular Weight:136.19

50-00-0 Synthesis

50-00-0
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$10.00/25g

620-19-9 Synthesis

620-19-9
268 suppliers
$8.00/25g

1875-89-4
166 suppliers
$20.00/1g

Yield:1875-89-4 83%

Reaction Conditions:

Stage #1:1-chloromethyl-3-methyl-benzene with chloro-trimethyl-silane;ethylene dibromide;zinc in tetrahydrofuran at 70; for 2 h;Schlenk technique;Inert atmosphere;
Stage #2:formaldehyd in tetrahydrofuran at 70; for 6 h;Schlenk technique;Inert atmosphere;

Steps:

Phenethyl alcohol (3a)
General procedure: Phenethyl alcohol (3a) A two neck Schlenk flask equipped with a magnetic stirring bar and septum was heated with heat gun (~400 °C) for 10 min under high vacuum. After cooling to room temperature, the flask was flushed with argon (3 times). Zn-dust (654 mg, 2.0 equiv, 10.0 mmol) was added followed by THF (20 mL). 1,2-Dibromoethane (5 mol%) was added and the reaction mixture was heated until ebullition occurs. After cooling to rt, chlorotrimethylsilane (1 mol%) was added and the mixture was heated again till ebullition occurs. The flask was again cooled to rt and benzyl chloride (633 mg, 5.0 mmol, 1 equiv) was added as a solution in THF (10 mL) and it was heated at 70 °C for 2 h and cooled to rt. Paraformaldehyde (450 mg, 3.0 equiv. 15.0 mmol) was slowly added at rt and the flask was again heated at 70 °C for 6 h. The solution was cooled to rt and saturated NH₄Cl solution was added. The phases were separated and the aqueous layer was extracted with ethyl acetate (100 mL). The combined organic layer was washed with water (20 mL), brine (10 mL) and then dried over Na₂SO₄. The solvents were evaporated under reduced pressure and the residue was purified by silica gel column chromatography using cyclohexane or cyclohexane/ethyl acetate as an eluent to obtain phenethyl alcohol (3a) (510 mg, 83%) as a colourless liquid.

References:

Bhatt;Samant;Pednekar, Suhas [Synthetic Communications,2017,vol. 47,# 10,p. 968 - 974] Location in patent:supporting information

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766-82-5 Synthesis