ChemicalBook CAS DataBase List 3-(2-NAPHTHYL)-1-PROPENE

3-(2-NAPHTHYL)-1-PROPENE synthesis

13synthesis methods

Product Name:3-(2-NAPHTHYL)-1-PROPENE
CAS Number:2489-87-4
Molecular formula:C13H12
Molecular Weight:168.23

580-13-2 Synthesis

580-13-2
507 suppliers
$6.00/1g

106-95-6 Synthesis

106-95-6
426 suppliers
$10.00/5g

2489-87-4
16 suppliers
$256.00/1g

Yield:2489-87-4 99%

Reaction Conditions:

Stage #1: 2-bromonaphthalenewith iodine;magnesium in tetrahydrofuran;Inert atmosphere;Reflux;
Stage #2: allyl bromide in tetrahydrofuran at 20;Reflux;
Stage #3: with ammonium chloride in tetrahydrofuran at 20;

Steps:

37

A two necks round bottom flask equipped with a condenser and a pressure compensated ad dition funnel was charged with magnesium turnings (28 mg, 0.96 mmol) and a few iodine pellets. The system was flamed under vacuum and cooled under argon atmosphere. Dry THF (0.6 mL) was added to the round bottom flask and the compensated addition funnel was charged with a solution of 2-bromonaphthalene (200 mg, 0.96 mmol) in dry THF (1 mL). This solution was slowly added to the suspension, which was heated under reflux for 2 h. The reaction mixture was cooled to room temperature and then it was treated with a solution of allyl bromide (0.09 mL, 1 mmol) in dry THF (0.5 mL). After heating under reflux for 2 h and cooling to room temperature saturated NH₄Cl was added. The organic layer was separated and the aqueous phase was ex- tracted with dichloromethane (x2). The combined organic extracts were dried (anh. Na₂SO₄), filtered and concentrated under reduced pressure. Purification by flash chromatography eluting with hexane gave 2-allylnaphthalene (31) (158 mg, 99%) as a colourless oil. ¹H NMR (300 MHz, CDCl₃) δ 7.91-7.85 (m, 3H, 3xArH), 7.71 (s, IH, ArH), 7.58-7.40 (m, 3H, 3xArH), 6.23-6.07 (m, IH, CH=CH₂), 5.28-5.19 (m, 2H, CH=CH₂), 3.63 (d, J= 7.8 Hz, 2H, CH₂) ppm. ¹³C NMR (75 MHz, CDCl₃) δ 137.5 (C), 137.3 (CH), 133.6 (C), 132.1 (C), 127.9 (CH), 127.6 (CH), 127.4 (CH), 127.3 (CH), 126.6 (CH), 125.9 (CH), 125.2 (CH), 116.0 (CH₂) and 40.3 (CH₂) ppm. MS (CI) m/z (%) 169 (MH⁺). HRMS calcd. for Ci₃Hi₃ (MH⁺): 169.1017, found, 169.1023.