ChemicalBook CAS DataBase List 4-ETHYL-4'-METHOXYBENZOPHENONE

4-ETHYL-4'-METHOXYBENZOPHENONE synthesis

5synthesis methods

Product Name:4-ETHYL-4'-METHOXYBENZOPHENONE
CAS Number:64357-92-2
Molecular formula:C16H16O2
Molecular Weight:240.3

16331-45-6
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100-66-3 Synthesis

100-66-3
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64357-92-2
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$294.00/1g

Yield:64357-92-2 100%

Reaction Conditions:

with aluminum (III) chloride in dichloromethane at 0 - 20; for 3.08 h;

Steps:

1.A

Example 1; Synthesis of (2^tS,3'R,4'S,5'S,6'R)-6-(4-ethylbenzyl)-6'-(hydroxymethyl)-3',4',5',6^l- tetrahydrospiro[chroman-4,2'-pyran]-3',4',5'-triol (Compound 12):; Part A: Synthesis of 4-(4-ethylbenzyl)phenol (3).; The overall synthetic scheme for phenol 3 is depicted in Scheme IA (see Figure 11).[0197] Synthesis of (4-ethylphenyl)(4-methoxyphenyl)methanone (1):[0198] To a solution of 4-ethylbenzoyl chloride (8.6 g, 51.0 mmol) in anhydrous DCM (200 mL) at -5 to 0 ⁰C, was added anisole (5.46 g, 50.5 mmol), followed by addition of aluminum chloride (7.0 g, 52.5 mmol) over 5 minutes. The resulting yellow reaction mixture was stirred at 0 ⁰C for 1 h and then at rt for 2 h. The reaction mixture was poured into ice water (300 mL), extracted with DCM (300 mL x 2). Combined DCM solution was washed with IM aqueous HCl (300 mL x 1), 2 N aqueous NaOH (200 ml x 1), brine (400 mL x 2), dried over MgSO₄ and evaporated to give the product, 12.2 g, yield 100%. ¹H NMR (300 MHz, CDCl₃) δ 7.80 (d, J=8.7 Hz, 2H), 7.68 (d, J=8.1 Hz, 2H), 7.27 (d, J=8.1 Hz, 2H), 6.93 (d, J=8.7 Hz, 2H), 3.87 (s, 3H), 2.71 (q, J=7.5 Hz, 2H), 1.28 (t, J=7.5 Hz, 3H). ESI-MS m/z 240.9 (M+H)⁺.

References:

WO2008/83200,2008,A2 Location in patent:Page/Page column 50-51