Home Cart Sign in  
Chemical Structure| 39192-49-9 Chemical Structure| 39192-49-9

Structure of 39192-49-9

Chemical Structure| 39192-49-9

*Storage: {[sel_prStorage]}

*Shipping: {[sel_prShipping]}

,{[proInfo.pro_purity]}

4.5 *For Research Use Only !

{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]} Purity: {[proInfo.pro_purity]}

Change View

Size Price VIP Price

US Stock

Global Stock

In Stock
{[ item.pr_size ]} Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate,item.pr_is_large_size_no_price, item.vip_usd) ]}

US Stock: ship in 0-1 business day
Global Stock: ship in 5-7 days

  • {[ item.pr_size ]}

In Stock

- +

Please Login or Create an Account to: See VIP prices and availability

US Stock: ship in 0-1 business day
Global Stock: ship in 2 weeks

  • 1-2 Day Shipping
  • High Quality
  • Technical Support
Product Citations

Alternative Products

Product Details of [ 39192-49-9 ]

CAS No. :39192-49-9
Formula : C11H9ClO5
M.W : 256.64
SMILES Code : O=C(Cl)C1=CC(OC(C)=O)=CC(OC(C)=O)=C1
MDL No. :MFCD24849661

Safety of [ 39192-49-9 ]

Application In Synthesis of [ 39192-49-9 ]

* 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.

  • Downstream synthetic route of [ 39192-49-9 ]

[ 39192-49-9 ] Synthesis Path-Downstream   1~3

  • 1
  • [ 35354-29-1 ]
  • [ 39192-49-9 ]
YieldReaction ConditionsOperation in experiment
98.2% With thionyl chloride; In dichloromethane;Reflux; Step 2: Diacetoxybenzoyl Chloride A 250 ml three-necked flask with magnetic stirrer, thermometer and condenser was charged with 15.4 g (64.7 mmol) of <strong>[35354-29-1]3,5-diacetoxybenzoic acid</strong>, 10 ml of thionyl chloride and 80 ml of CH2Cl2. The mixture was refluxed for 3-5 hours. Then the solvent and remaining thionyl chloride were distilled off. Fresh CH2Cl2 was added and distilled off again. The crude solid was dissolved in 120 ml toluene, and the solution was filtered. Evaporated the solvent out and dried the product at room temperature under 1 mbar. 16.3 g of 3,5-diacetoxybenzoyl chloride were obtained as a white solid. The yield was 98.2%.
98.2% With thionyl chloride; In dichloromethane;Reflux; Step 2: Diacetoxybenzoyl chloride A 250 ml three-necked flask with magnetic stirrer, thermometer and condenser was charged with 15.4 g (64.7 mmol) of <strong>[35354-29-1]3,5-diacetoxybenzoic acid</strong>, 10 ml of thionyl chloride and 80 ml of CH2Cl2. The mixture was refluxed for 3 to 5 hours. Then the solvent and remaining thionyl chloride were distilled off. Fresh CH2Cl2 was added and distilled off again. The crude solid was dissolved in 120 ml toluene, and the solution was filtered. Evaporated the solvent out and dried the product at room temperature under 1 mbar. 16.3 g of 3,5-diacetoxybenzoyl chloride were obtained as a white solid. The yield was 98.2 %.
95.5% With thionyl chloride;N,N-dimethyl-formamide; In toluene; at 20 - 80℃; for 2.25h; 6. Preparation of 3,5-diacetoxybenzoyl chloride To a mixture of <strong>[35354-29-1]3,5-diacetoxybenzoic acid</strong> (8.00 g, 33.59 mmol) and dimethylformamide (5 drops) in toluene was added freshly distilled thionylchloride (16 mL). The mixture was stirred for 15 min under nitrogen atmosphere at ambient temperature. Then it was refluxed for 2 h at 80 C. in a hot water bath. The excess thionyl chloride was evaporated in vacuo and toluene was added. Insoluble yellow solid was discarded. Toluene was evaporated in vacuo and gave 3,5-diacetoxybenzoyl chloride (8.23 g, 95.5%), which can be recrystallized from hexane. Data are: 1H NMR (CDCl3, 300 MHz) δ 7.75 (d, 2H), 7.29 (t, 1H), 2.34 (s, 6H); 13C NMR (CDCl3, 75 MHz) δ 168.8, 167.0, 151.4, 135.3, 122.8, 122.0, 21.2; mp=89.5-91 C.; HRMS (EI+) found 256.0130 M+, calcd 256.0139 for C11H9O5Cl; Anal. Calcd for C11H9O5Cl: C, 51.48; H, 3.53. Found: C, 51.60; H, 3.68.
In thionyl chloride; The obtained <strong>[35354-29-1]3,5-diacetoxybenzoic acid</strong> (2.38 g, 10 mM) was dissolved in 5 ml of SOCl2 and the solution was heated under reflux at 80 C. for 1 hour. The solvent SOCl2 was distilled off under reduced pressure to yield 3,5-diacetoxybenzoyl chloride (2.44 g).
With thionyl chloride; In benzene; 42 g of <strong>[35354-29-1]3,5-diacetoxybenzoic acid</strong> are heated under reflux for 5 hours with 300 ml of benzene and 26 ml of thionyl chloride. The reaction mixture is concentrated by evaporation and the residue is taken up in benzene and again concentrated by evaporation. 3,5-diacetoxybenzoyl chloride having a melting point of 85-87 is thus obtained. In a manner analogous to that described in Example 1, 1-[2-(4-chlorophenyl)-ethyl]-4-(3,5-diacetoxybenzoyl)-piperazine hydrochloride having a melting point of 220 (decomposition) is obtained from 3,5-diacetoxybenzoyl chloride.
With thionyl chloride; In N,N-dimethyl-formamide; toluene; at 100℃; for 3h;Inert atmosphere; A suspension of <strong>[35354-29-1]3,5-diacetoxybenzoic acid</strong> (8.022 g, 33.71 mmol) in a mixture of toluene (130 mL),DMF (500 μL) and thionyl chloride (16.00 mL, 220.6 mmol) was heated at 100 C for three hours underan argon gas atmosphere. The solvents were removed by vacuum distillation and the residue re-suspendedin toluene (85 mL) and sonicated under vacuum to remove dissolved gases. 4-Acetoxystyrene (5.74 mL,37.5 mmol), N-ethylmorpholine (4.31 mL, 33.9 mmol) and palladium diacetate (35 mg, 0.16 mmol,0.46 mol %) were added and the reaction heated to reflux for 2 h. Further palladium diacetate (116 mg,0.52 mmol, 1.54 mol %) was added and the reaction left to reflux overnight. On return to roomtemperature, ethyl acetate (500 mL) was added, the solution washed with 0.1 M aq. HCl (2 × 300 mL)and water (300 mL) and then dried and evaporated to return a brown solid. Purification with columnchromatography (isocratically eluted with 2:1 Et2O/hexane) gave 7.888 g of a white solid, shown by1H-NMR spectroscopy to be predominantly the desired adduct. Further chromatography (gradienteluted starting with 4:1 hexane/EtOAc and finishing with 2:1 hexane/EtOAc) returned pure (E)-3,4′,5-triacetoxystilbene (6.071 g, 51%) as a white solid.
With thionyl chloride; at 78℃; for 4h; General procedure: 3,4,5-triacetoxybenzoic acid 4a (2000 mg, 6.756 mmol) wasdissolved in SOCl2 (8000 mg, 67.244 mmol). The solution was thenheated under reflux at 78 C for 4 h. The solvent was removed usinga rotary evaporator under reduced pressure to yield white solid.Yielding 99% compound 5a (2100 mg) as a white solid. Compounds5b-c and 7a were synthesized following the procedure of preparation5a.

  • 2
  • [ 39192-49-9 ]
  • [ 99-10-5 ]
  • [ 35354-29-1 ]
  • [ 7440-05-3 ]
  • [ 57179-37-0 ]
YieldReaction ConditionsOperation in experiment
With thionyl chloride; acetic anhydride; In pyridine; CH2 Cl; 5,5-dimethyl-1,3-cyclohexadiene; hydrogen; benzene; EXAMPLE 1 3,5-Diacetoxybenzaldehyde A total of 82.4 ml of acetic anhydride (89.8 g, 0.88 mole) was added in small portions to a stirring mixture of 61.7 g of 3,5-dihydroxybenzoic acid (0.4 mole) in 130 ml of pyridine. After the addition was complete, the reaction mixture was left stirring for 15 hours at ambient temperature. The pyridine was removed by evaporation in vacuo. The residue was taken up in CH2 Cl 2 and washed several times with 6N HCl and water and dried (Na2 SO4). Removal of solvent under reduced pressure left 68.2 g (72%) of <strong>[35354-29-1]3,5-diacetoxybenzoic acid</strong> which was used without further purification. A stirring mixture of 68.2 g (0.29 mole) of <strong>[35354-29-1]3,5-diacetoxybenzoic acid</strong> and 21 ml (0.29 mole) of thionyl chloride in 150 ml of dry benzene was heated in an oil bath at 80-90 C. for 2 hours. After cooling the benzene was removed in vacuo to leave 3,5-diacetoxybenzoyl chloride as a tan, solid which was recrystallized from cyclohexane as colorless crystals, mp 87-89 C., 61.8 g (83% yield). A mixture of 61.8 g (0.24 mole) of 3,5-diacetoxybenzoyl chloride and 6 g of 5% palladium on BaSO4 in 200 ml of dry xylene was efficiently stirred while bubbling in hydrogen gas. The reaction mixture was slowly heated to 115 C. in an oil bath and the heating was continued until the evolution of HCl gas ceased (approximately 5 hours). After cooling, the mixture was filtered and the xylene was removed in vacuo to leave 48 g (90%) of 3,5-diacetoxybenzaldehyde which was used without further purification in subsequent reactions.
  • 3
  • N,N-DMF [ No CAS ]
  • [ 35354-29-1 ]
  • [ 39192-49-9 ]
YieldReaction ConditionsOperation in experiment
With thionyl chloride; In hexane; toluene; Example 23 3,5-Diacetoxy benzoyl chloride (23). A suspension of <strong>[35354-29-1]3,5-diacetoxybenzoic acid</strong> in dry toluene, N,N-DMF and thionyl chloride was heated at 100 C. for three hours under a nitrogen atmosphere. The solvents were removed by vacuum distillation and the remaining viscous liquid treated with hexane to precipitate a yellow solid. Hexane was removed by rotary evaporation to give a pale yellow powder. This compound was immediately on-reacted. Rf 0.88 (2:1 EtOAc/hexane). Rf 0.88 (2:1 EtOAc/hexane).
 

Historical Records