ChemicalBook CAS DataBase List (±)-trans-1,3-Diphenylallyl acetate

(±)-trans-1,3-Diphenylallyl acetate synthesis

9synthesis methods

Product Name:(±)-trans-1,3-Diphenylallyl acetate
CAS Number:87751-69-7
Molecular formula:C17H16O2
Molecular Weight:252.31

62668-02-4 Synthesis

62668-02-4
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$20.00/1g

75-36-5 Synthesis

75-36-5
589 suppliers
$17.92/100G

87751-69-7
11 suppliers
$82.59/1g

Yield:87751-69-7 95%

Reaction Conditions:

with triethylamine in dichloromethane at 0 - 20; for 4 h;

Steps:

4.5.1. (±)-(E)-1,3-diphenylallyl acetate (19)

Prepared according to the literature procedure [22]. (±)-(E)-1,3- Diphenylallyl alcohol (28.6 mmol, 6.0 g, 1.0 equiv.) was dissolved in anhydrous CH2Cl2 (70 mL) and Et3N (34.8 mmol, 4.83 mL, 1.22 equiv.) was added. The mixture was cooled to 0 °C via ice bath, and a solution of acetyl chloride (34.3 mmol, 2.46 mL, 1.20 equiv.) in anhydrous CH2Cl2 was slowly added. Then, the solution was allowed to warm up to room temperature and it was stirred for 4 h. The reaction mixture was washed with 2 M NaOH (3x), water (2x) and brine (2x) successively, dried over Na2SO4, filtered and evaporated. The crude product was purified by Kugelrohr distillation (0.35 mBar, 150-170 °C) to obtain the product 19 as a light-yellow oil (6.84 g, 95% yield). 1H NMR (400 MHz, CDCl3)d: 7.37-7.21 (m, 10H, H-arom), 6.56 (d, J = 16.0 Hz, 1H, arom-CH=CH), 6.37 (d, J = 8.0 Hz, 1H, arom-CH=CH), 6.27 (dd, J = 16.0 Hz, 4.0 Hz, 1H, arom-CH), 2.09 (s, 3H, CH3-CO); 13C NMR (100 MHz, CDCl3)d: 170.3 (CH3-CO), 139.5 (C-arom), 136.4 (arom-CH), 132.8 (arom-CH=CH), 128.9 (C-arom), 128.8 (C-arom), 128.4 (C-arom), 128.3 (C-arom), 127.7 (C-arom), 127.3 (arom-CH=CH), 126.9 (C-arom), 76.4 (arom- CH), 21.6 (CH3-CO).

References:

Pálv?lgyi, ádám Márk;Schnürch, Michael;Bica-Schr?der, Katharina [Tetrahedron,2020,vol. 76,# 51,art. no. 131246]

62668-02-4 Synthesis

62668-02-4
83 suppliers
$20.00/1g