ChemicalBook CAS DataBase List Methyl 2-(2-forMyl-4-nitrophenoxy)hexanoate

Methyl 2-(2-forMyl-4-nitrophenoxy)hexanoate synthesis

4synthesis methods

Product Name:Methyl 2-(2-forMyl-4-nitrophenoxy)hexanoate
CAS Number:335153-23-6
Molecular formula:C14H17NO6
Molecular Weight:295.29

138320-26-0 Synthesis

methyl 2-(2-formylphenoxy)hexanoate(WXG00679)

138320-26-0
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Methyl 2-(2-forMyl-4-nitrophenoxy)hexanoate

335153-23-6
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Yield:335153-23-6 92.4%

Reaction Conditions:

Stage #1: methyl 2-(2-formylphenoxy)hexanoatewith sulfuric acid at 5; for 0.25 h;
Stage #2: at 5; for 2 h;

Steps:

3 EXAMPLE 3, Preparation of methyl 2-(2-formyl-4-nitro-phenoxy)hexanoate

EXAMPLE 3 [00324] Preparation of methyl 2-(2-formyl-4-nitro-phenoxy)hexanoate [00325] Methyl 2-(2-formyl-4-nitro-phenoxy)-hexanoate can be prepared as follows: [00326] 123 g of 96% concentrated sulphuric acid was charged into a 250 ml four-neck reactor provided with a Teflon half moon paddle stirrer, a thermometer, a 50 ml dropping funnel, a cooling coil and a nitrogen inlet. [00327] The reaction medium was cooled to a temperature of close to 5° C. then 30 g (0.12 mole) of methyl 2-(2-formylphenoxy)-hexanoate was added at the same temperature. [00328] After stirring for 15 minutes, 15.9 g (0.126 mole) of nitrating mixture (50/50) was added over 2 hours, keeping the reaction medium close to 5° C., then 76.9 g of ice was added over 30 minutes, leading to an H₂SO₄titre of 60%. [00329] The reaction mixture was filtered through a n^o3 frit after stirring for 10 minutes. [00330] The crude product obtained was dissolved in 100 ml of dichloromethane and washed with twice 50 ml of water. [00331] The decanted organic phase was concentrated in a rotary evaporator at 20° C. to 70° C. in 20 mm of mercury (duration: 2 hours). [00332] 32.7 g of a beige yellow solid product was obtained, giving a yield of methyl 2-(2-formyl-4-nitro-phenoxy)-hexanoate of 92.4%, titrating at 96.7% by gas chromatography. [00333] It had the following NMR spectrum: [00334] ¹H NMR (DMSO-d6): δ0.91 (t, 3H, CH₃); 1.38 (m, 2H, CH₂-CH₃); 1.51 (m, 2H, CH₂-CH₂-CH₃); 2.02 (m, 2H, CH₂-CH); 5.24 (t, 1H, CH); 7.34 (d, J=9 Hz, 1H, ArH); 8.44 (d, J=2 Hz, 1H, ArH); 8.47 (dd, J=9 Hz, J=2 Hz, 1H, ArH); 10.42 (s, 1H, CHO); 13.45 (broad peak, 1H, COOH).