* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
With hydrogenchloride; sodium hydroxide In dichloromethane; water; 1,3,5-trimethyl-benzene
EXAMPLE 10 6-Methoxy-2-propionylnaphthalene 29.3 Grams of 5-bromo-6-methoxy-2-propionylnaphthalene are dissolved in 100 ml of anhydrous methylene chloride and in 20.8 ml of mesitylene. 20 Grams of anhydrous aluminum chloride are added portionwise to the reaction mixture cooled to -5°C under strong stirring, while keeping the temperature below 20°C. The reaction mixture is kept for over 3 hours under stirring at room temperature, then it is slowly poured under strong stirring into a mixture made of 110 g of ice and of 35 ml of a 35percent (w/v) aqueous solution of hydrochloric acid. The layers are separated after 15 minutes of stirring and the aqueous layer is discarded. The organic layer first is twice washed with 50 ml of a 6 N aqueous solution of hydrochloric acid and then with 50 ml of water. The organic solution is then added with 50 ml of water and the pH is brought to 12 by means of a 30percent (w/v) aqueous solution of sodium hydroxide. The aqueous phase is discarded while the organic phase is dried over anhydrous sodium sulfate and evaporated to dryness under vacuum. The residue is crystallized by n-heptane obtaining 20.2 g of product with a yield equal to 94.3percent.
94.3%
With hydrogenchloride; sodium hydroxide In dichloromethane; water; 1,3,5-trimethyl-benzene
EXAMPLE 10 6-Methoxy-2-propionylnaphthalene 29.3 Grams of 5-bromo-6-methoxy-2-propionylnaphthalene are dissolved in 100 ml of anhydrous methylene chloride and in 20.8 ml of mesitylene. 20 Grams of anhydrous aluminum chloride are added portionwise to the reaction mixture cooled to -5° C. under strong stirring, while keeping the temperature below 20° C. The reaction mixture is kept for over 3 hours under stirring at room temperature, then it is slowly poured under strong stirring into a mixture made of 110 g of ice and of 35 ml of a 35percent (w/v) aqueous solution of hydrochloric acid. The layers are separated after 15 minutes of stirring and the aqueous layer is discarded. The organic layer first is twice washed with 50 ml of a 6N aqueous solution of hydrochloric acid and then with 50 ml of water. The organic solution is then added with 50 ml of water and the pH is brought to 12 by means of a 30percent (w/v) aqueous solution of sodium hydroxide. The aqueous phase is discarded while the organic phase is dried over anhydrous sodium sulfate and evaporated to dryness under vacuum. The residue is crystallized by n-heptane obtaining 20.2 g of product with a yield equal to 94.3percent.
In the is provided with an agitator, reflux condenser, thermometer, dropping funnel in the reaction container, adding triethylamine to 310 ml, stannous chloride 0.65mol, control the stirring speed 190rpm, reducing the temperature of the solution to 5 °C, β-naphthyl methyl ether is slowly added (2) 0.65mol, adds by drops third amide (3) 0.47mol, dropping time control, in 80 min, maintaining the temperature of the solution reaction 9h, raising the temperature of the solution to 19 °C, standing 22h, the reactants are poured into the 1.8L the mass fraction of 25percent sodium bisulfite solution, control the temperature of the solution in the 5 °C, steam distillation, until completely distilled until the triethylamine, control the stirring speed 130rpm, let solution of natural cooling, solidifying oily substance, filtering, potassium nitrate solution, anhydrous calcium sulfate dehydration, in the mass fraction is 92percent recrystallized in cyclohexane solution, to get the yellow solid 6-methoxy-2-c acyl-naphthaline 85.49g, yield 85percent.
Reference：
[1] Patent: CN105439833, 2016, A, . Location in patent: Paragraph 0015; 0016
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[ 93-04-9 ]
[ 79-03-8 ]
[ 2700-47-2 ]
Reference：
[1] Tetrahedron, 1994, vol. 50, # 4, p. 1243 - 1260
[2] Chemistry - A European Journal, 2016, vol. 22, # 45, p. 16072 - 16077
[3] Recueil des Travaux Chimiques des Pays-Bas, 1949, vol. 68, p. 781,785
[4] Journal of the Chemical Society, 1934, p. 864,866
[5] Bulletin de la Societe Chimique de France, 1948, p. 711,715
[6] Proceedings - Indian Academy of Sciences, Section A, 1946, vol. <A> 24, p. 382,385
[7] Bulletin de la Societe Chimique de France, 1948, p. 711,715
[8] Patent: US4670603, 1987, A,
[9] Patent: EP176142, 1991, B1,
[10] Pr.roy.Soc.<B>, 1942, vol. 130, p. 435,444
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[ 114703-08-1 ]
[ 2700-47-2 ]
Reference：
[1] Advanced Synthesis and Catalysis, 2015, vol. 357, # 8, p. 1721 - 1731
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[ 5111-65-9 ]
[ 79-03-8 ]
[ 2700-47-2 ]
Reference：
[1] Bioorganic and Medicinal Chemistry Letters, 2006, vol. 16, # 10, p. 2729 - 2733
With aqueous HBr; sodium hydrogencarbonate; In water; acetic acid;
STR16 To a solution of 10 g of 2-methoxy-6-propionyl-naphthalene, prepared according to J. Chem. Soc. (1934), p. 864, in acetic acid (45 ml) and kept under reflux, 47 ml of aqueous HBr (48% by weight) is added during a three-hour time period. The resulting suspension is poured onto 500 g of crushed ice; the formed tars are left in the reaction flask. A suspension is obtained which is filtered on a Buchner filter. The solid material is washed with 100 ml of water, 50 ml of saturated aqueous solution of NaHCO3, and then with 50 ml of water. After drying in air and in an oven at 60 C. for 10 hours, 5.3 g of pink-white product is obtained with the following characteristics: m.p. 158-9 C. (uncorrected); 1 H-NMR (200 MHz, CDCl3 -TMS) delta (ppm); 1.18 (3H, t, CH3); 3.1 (2H, q, CH2); 7.1-7.3 (2H, m, aromatic H); 7.75 (1H, d, aromatic H); 7.85-8.05 (2H, m, aromatic H); 8.53 (1H, s, aromatic H); 8.95-9.3 (1H, bs, hydroxy H).
With chloro-trimethyl-silane; phenyltrimethylammonium tribromide; In toluene; at 15 - 20℃;
1700 g of toluene was placed in the reaction flask. Trimethylchlorosilane 5g, Stir, Add 610 g (1.62 mol) of PTT (phenyltrimethylammonium tribromide), Add 6-methoxy-2-propionyl naphthalene 330g (1.54 mol), Temperature control 15-20 C reaction, After the reaction, the water is washed and layered. A toluene solution was obtained.
EXAMPLE 3 1-(6'-methoxy-2'-naphthyl)-propan-1-one To 225 g of anhydrous hydrofluoric acid, 49.5 g (0.57 mol) of propionyl chloride and then 70 g (0.44 mol) of 2-methoxy-naphthalene in 90 g of anhydrous hydrofluoric acid were added at 19 C. The reaction mixture was maintained at 40 C. for 71 hours and then worked up as disclosed in Example 1. Yield, 70 g (73%).
70 g (73%)
In hydrogen fluoride;
Example 3 1-(6'-methoxy-2'-naphthyl)-propan-1-one To 225 g of anhydrous hydrofluoric acid, 49.5 g (0.57 mol) of propionyl chloride and then 70 g (0.44 mol) of 2-methoxy-naphthalene in 90 g of anhydrous hydrofluoric acid were added at 19C. The reaction mixture was maintained at 40C for 71 hours and then worked up as disclosed in Example 1. Yield, 70 g (73%).
100 g
With aluminum (III) chloride; In nitromethane; 1,2-dichloro-ethane; at 0 - 20℃;
300 g of dichloroethane was placed in the reaction flask. 10g nitromethane, 100 g (0.632 mol) of beta-naphthylmethyl ether was added with stirring. 95g (0.713mol) aluminum trichloride, Stir and cool to 0-5 C, Add propionyl chloride 63g (0.683mol), Insulation reaction for 2 hours, Warming to room temperature and continuing the reaction until the reaction is complete. Add 500g of ice water to stir. Layered, The organic phase is added to 300g of water for washing. Layered, Wash with 150g of 6% sodium hydroxide solution, Layered, The organic layer is distilled off, Add 20g of methanol, Reflux, Cooling and crystallization, Filtered 6-methoxy-2-propionyl naphthalene 100 g.
EXAMPLE 1 A solution of bromine (8.95 g; 0.056 moles) in 1,2-dichloroethane (10 ml) is added, under nitrogen at 15 C., to a solution of 1-(6-methoxy-2-naphthyl)-propan-1-one (6 g; 0.028 moles) in 1,2-dichloroethane (50 ml). When the bromine has been completely consumed, 1-(6-methoxy-2-naphthyl)-propan-1-one (6 g; 0.028 moles) is added to the solution. The reaction mixture is kept at 15 C. for 168 hours, and is then diluted with 1,2-dichloroethane (10 ml). The solution thus obtained is washed with water and dried with sodium sulphate. The solvent is evaporated under vacuum to yield 2-bromo-1-(6-methoxy-2-naphthyl)-propan-1-one (16.90 g; HPLC titre=78%; 0.045 moles; Yield 80%).
The reaction is followed by GLC analysis. After 24 hours 95% of the starting substance has been converted, the 2-methoxy-6-propionyl-naphthalene being formed with a yield of 90% on the converted 2-methoxy-naphthalene. The reaction mixture is poured into water (212 g) cooled to 0 C. The organic phase is separated and dried over anhydrous Na2 SO4.
80%
The 2-methoxy-6-propionyl-naphthalene is obtained by evaporating the solvent, after which it is crystallized from methanol to show a M.P. of 114-115 C. an a yield of 80%.
EXAMPLE 2 The reaction of Example 1 is repeated using 0.64 moles of AlCl3 and 0.32 moles of nitrobenzene, the reactant quantities being as given. After 6 hours the crude reaction mixture already contains 84% of 2-methoxy-6-propionyl-naphthalene, which is isolated as described in Example 1.
61
1-<6-methoxy-1.2.3.4-tetrahydro-naphthyl-(2)>-propanone-(1)[ No CAS ]
(S)-2-(6-Methoxy-naphthalen-2-yl)-propionic acid (2R,3R,4R,5R)-2,3,4,5,6-pentahydroxy-hexyl ester[ No CAS ]
(S)-2-(6-Methoxy-naphthalen-2-yl)-propionic acid (2R,3R,4R,5R)-2,3,4,5-tetrahydroxy-6-[(S)-2-(6-methoxy-naphthalen-2-yl)-propionyloxy]-hexyl ester[ No CAS ]
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