ChemicalBook CAS DataBase List 7,8,9,10-TETRAHYDRO-BENZO[A]PYREN-7-OL

7,8,9,10-TETRAHYDRO-BENZO[A]PYREN-7-OL synthesis

11synthesis methods

Product Name:7,8,9,10-TETRAHYDRO-BENZO[A]PYREN-7-OL
CAS Number:6272-55-5
Molecular formula:C20H16O
Molecular Weight:272.34

3331-46-2
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$131.00/250mg

6272-55-5
42 suppliers
$43.00/250mg

Yield:6272-55-5 11.1 g

Reaction Conditions:

with sodium tetrahydridoborate in tetrahydrofuran;methanol at 20; for 1 h;

Steps:

7-Hydroxy-7,8,9,10-tetrahydrobenzo[a]pyrene (4)

The crude product 3 (12.24 g, 45.28 mmol) was dissolved in THF (150 mL, anhydrous)and CH3OH (50 mL, anhydrous) in a 500-mL round-bottom flask. NaBH4 (1.71 g,45.28 mmol) was added over 15 min, and then the reaction mixture was stirred at roomtemperature for 45 min. After checking the full conversion of 3 by TLC, the reactionwas quenched with 1N HCl, and most of the solvent was removed under reduced pressure.The residue was dissolved in CH2Cl2 (250 mL). The solution was washed withwater and then dried over MgSO4. After filtration, the solvent was evaporated underreduced pressure to afford the crude product 4 (11.10 g, 40.76 mmol, 90%). Brown-yellowsolid. 1H NMR (400 MHz, CDCl3): d 2.03-2.12 (m, 3H, CH2 and OH), 2.19-2.29(m, 2H, CH2), 3.35 (dt, J6.5, 17.06 Hz, 1H, ArCHH), 3.53 (dt, J5.8, 17.36 Hz, 1H,ArCHH), 5.22 (t, J4.7 Hz, 1H, CHOH), 7.95-8.00 (m, 3H, Ar), 8.09-8.17 (m, 3H, Ar),8.23 (d, J9.3 Hz, 1H, Ar), 8.28 (s, 1H, Ar); 13C NMR (100 MHz, CDCl3): d 18.8(CH2), 26.3 (CH2), 32.2 (CH2), 69.2 (CH), 123.0 (CH), 124.2 (C), 124.6 (C), 124.90(CH), 124.95 (CH), 125.1 (CH), 125.8 (CH), 126.7 (CH), 127.4 (CH), 127.5 (CH), 128.8(C), 129.6 (C), 130.8 (C), 130.9 (C), 131.4 (C), 136.7 (C) ppm.

References:

Kurono, Nobuhito;Iwashita, Yuji;Sugimura, Haruhiko [Organic Preparations and Procedures International,2022,vol. 54,# 5,p. 457 - 464]