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[ CAS No. 6836-23-3 ] {[proInfo.proName]}

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Chemical Structure| 6836-23-3
Chemical Structure| 6836-23-3
Structure of 6836-23-3 * Storage: {[proInfo.prStorage]}
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Product Details of [ 6836-23-3 ]

CAS No. :6836-23-3 MDL No. :MFCD27956331
Formula : C13H11ClO2 Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 234.68 Pubchem ID :-
Synonyms :

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Application In Synthesis of [ 6836-23-3 ]

* 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 [ 6836-23-3 ]

[ 6836-23-3 ] Synthesis Path-Downstream   1~5

  • 1
  • [ 6836-22-2 ]
  • [ 6836-23-3 ]
YieldReaction ConditionsOperation in experiment
99% With thionyl chloride; In dichloromethane; N,N-dimethyl-formamide; at 35 - 40℃; A mixture of 2-(7-methoxy-1 -naphthyl) acetic acid (100g), Dichloro methane(500 ml). Dimethyl formamide(l ml), thionyl chloride 65.98 g was stirred and heated to 35 to 40 C 1 hr. The solvent was distilled out completely under vacuum. Toluene (800 ml) was added to the residue, ammonia gas was purged at 0-5 C till pH 10-1 1. After the completion of reaction, reaction mixture was heated at 45-50C. Cooled the reaction mass, filtered the solid, washed with toluene. The materials so obtained, Phosphorous oxychloride (85.08 g) and toluene (500 ml) was stirred and heated at 85 C for 2 hrs. The mixture was partitioned between water and toluene. Organic phase was washed with aq. NaHCO3 solution. The solvent was distilled out completely under vacuum. Toluene (50 ml), methanol (200 ml) was added to the residue and cooled 5- 10 C. Filtered the solid and washed with methanol and dried to obtained 2-(7-methoxynaphthyl) acetonitrile (Yield 91 %, HPLC purity 99.5%).
With thionyl chloride; In chloroform; at 20 - 40℃; 7-Methoxy-naphthalen-1-yl)-acetyl chloride): At ambient temperature, thionyl chloride (13.1 g, 110.6 mmol) was added dropwise to a suspension of (7-methoxy-naphthalen-1-yl)-acetic acid (2.38 g, 11.1 mmol) in chloroform (30 mL). The reaction mixture was heated and maintained at about 40 C. until (7-methoxy-naphthalen-1-yl)-acetic acid was no longer detected by TLC. The solvent and excess thionyl chloride were removed in vacuo to give the title product as a brown oil, which was used directly in next step without further purification.
With thionyl chloride; In dichloromethane; for 2.0h;Reflux; Reference example 4: The preparation of 7-methoxy-1-naphthaleneacetamide 50g 7-methoxy-1-naphthaleneacetic acid was added into 750ml dichloromethane and heated to dissolve the same. Thionyl chloride was slowly added in drops while kept in reflux state. The reaction was refluxed for further 2h after the completion of addition. After completion of the reaction, the reaction solution was vacuum evaporated to obtain brown-red oil. It was cooled to solidify by external ice water. The obtained solid was dissolved in 500ml ethyl acetate, and cooled by external ice saline. 47.2my ammonia water was slowly added in drops, resulting in a large amount of light yellow solid being precipitated. It was filtered and dried to obtain 49.8g crude product. Recrystallization was carried out by using 747ml 95% ethanol and 37.3g activated carbon to obtain 46g refined product with the mp of 201-202C. The yield is 92.4%.
With oxalyl dichloride; In dichloromethane; at 0℃; for 0.5h; Preparation of 8-methoxyacenaphthylen- 1 (2H)-one (Compound 20-3) [003601 A solution of 2-(7-methoxynaphthalen- 1 -yl)acetic acid (Compound 20-1) (1 g, 4.63 mmol) in dichloromethane (20 mL) at 0C was added oxalyl chloride(700 mg, 5.56 mmol) dropwise. The mixture was stirred at 0C for 0.5 h, Then crashed aluminum chloride (1.35 g, 10 mmol) was added at 0 C in 15 minutes. The dark mixture was stirred at 0 C to room temperature for 2 hours. The mixture was poured into ice-water (20 mL). The mixture was extracted with dichloromethane (30 mL x 3).The combined organic layer was washed with brine (20 mL) and dried over sodium sulfate, filtered. The filtration was concentrated in vacuum to give the crude product as a pale yellow solid. The crude product was purified by chromatography to give Compound 20-3 as a white solid (800 mg, 87 %, petrol ether/ethyl acetate = 100/ 1 - 50/ 1). MS m/z 199[M+1]. ?H NMR (400 MHz, CDC13) 5 8.09-8.07 (d, J= 8.8 Hz 1H), 7.75-7.31(d, J= 8.0 Hz 1H), 7.47-7.41 (m, 2H), 7.36-7.34 (d, J= 8.8 Hz 1H), 4.15(s, 3H), 3.80(s, 2H).

  • 4
  • [ 6836-21-1 ]
  • [ 6836-23-3 ]
  • 5
  • [ 6836-23-3 ]
  • [ 138113-09-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: ammonia / ethyl acetate; water / Cooling with ice 2: triethylamine; trifluoroacetic anhydride / tetrahydrofuran / 20 °C / Cooling with ice 3: hydrogen; ammonia / ethanol; water / 12 h / 60 °C / 228015 Torr / Autoclave
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