ChemicalBook CAS DataBase List (4-Vinylphenyl)methanol

(4-Vinylphenyl)methanol synthesis

11synthesis methods

Product Name:(4-Vinylphenyl)methanol
CAS Number:1074-61-9
Molecular formula:C9H10O
Molecular Weight:134.18

1075-49-6

1074-61-9

The general procedure for the synthesis of (4-vinylphenyl)methanol from 4-vinylbenzoic acid was as follows: 4-vinylbenzoic acid (500 mg, 3.37 mmol) was dissolved in Et2O (25 mL) according to the methodology described in the literature [31] and slowly added dropwise to a 0 °C LiAlH4 (758 mg, 19.97 mmol) in THF (80 mL) suspension. The reaction mixture was gradually warmed to room temperature and stirred continuously for 1 hour. Upon completion of the reaction, water (256 μL), 10 wt% NaOH solution (512 μL) and water (768 μL) were added slowly and sequentially to quench the reaction. The mixture was vigorously stirred until a white solid was formed. The crude reaction mixture was filtered and the supernatant was dried with anhydrous Na2SO4 and concentrated under reduced pressure. The resulting oil was purified by silica gel column chromatography with hexane:EtOAc (4:1) as eluent to afford the target product (4-vinylphenyl)methanol (280 mg, 62%) as a colorless oil. The physical and spectral data of the product were in agreement with those reported in the literature [31].1H NMR (CDCl3, 500 MHz) δ: 4.66 (s, 2H), 5.24 (d, J = 11.5 Hz, 1H), 5.73 (d, J = 18.5 Hz, 1H), 6.69-6.75 (dd, J = 11.0, 6.5 Hz, 1H), 7.31 (d , J = 8.0 Hz, 2H), 7.39 (d, J = 8.0 Hz, 2H).

1076-96-6 Synthesis

1076-96-6
133 suppliers
$31.00/250mg

1074-61-9
112 suppliers
$20.00/100mg

Yield:1074-61-9 82%

Reaction Conditions:

Stage #1: methyl 4-vinylbenzoatewith 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane;lithium tert-butoxide in tetrahydrofuran at 100; for 24 h;Inert atmosphere;
Stage #2: with methanol;sodium hydroxide in tetrahydrofuran at 20;Inert atmosphere;

Steps:

10 The preparation of (4-vinylphenyl) methanol, the structural formula is as follows:

Under nitrogen protection, the raw materials methyl 4-vinylbenzoate (1 mmol) and pinacolborane (2.5 mmol) were added, the catalyst LiOtBu (0.05mol) and the solvent tetrahydrofuran (1.0mL) were reacted at 100°C for 24h, subsequently, 2 mol/L NaOH/MeOH solution (ie, 2 mol of sodium hydroxide per liter of methanol) was added, and the mixture was stirred at room temperature overnight, and the product separation yield was 82%.

References:

CN113860990,2021,A Location in patent:Paragraph 0079-0084

1075-49-6 Synthesis

1075-49-6
318 suppliers
$17.00/1g

1074-61-9
112 suppliers
$20.00/100mg

References