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[ CAS No. 4841-22-9 ]

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2D
Chemical Structure| 4841-22-9
Chemical Structure| 4841-22-9
Structure of 4841-22-9 *Storage: {[proInfo.prStorage]}

Quality Control of [ 4841-22-9 ]

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Related Doc. of [ 4841-22-9 ]

SDS

Product Details of [ 4841-22-9 ]

CAS No. :4841-22-9MDL No. :MFCD00063317
Formula :C9H9ClO3Boiling Point :267°C at 760 mmHg
Linear Structure Formula :-InChI Key :OSGZHKYFZSNKRI-UHFFFAOYSA-N
M.W :200.62Pubchem ID :96277
Synonyms :

Computed Properties of [ 4841-22-9 ]

TPSA : 35.5 H-Bond Acceptor Count : 3
XLogP3 : - H-Bond Donor Count : 0
SP3 : 0.22 Rotatable Bond Count : 4

Safety of [ 4841-22-9 ]

Signal Word:WarningClassN/A
Precautionary Statements:P261-P305+P351+P338UN#:N/A
Hazard Statements:H315-H319-H335Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 4841-22-9 ]

  • Upstream synthesis route of [ 4841-22-9 ]
  • Downstream synthetic route of [ 4841-22-9 ]

[ 4841-22-9 ] Synthesis Path-Upstream   1~4

  • 1
  • [ 96-32-2 ]
  • [ 106-48-9 ]
  • [ 4841-22-9 ]
YieldReaction ConditionsOperation in experiment
96.5%
Stage #1: With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 0.03 h;
Stage #2: at 80℃; for 4.00 h;
To a solution of 4-chlorophenol (15 g, 1 16.67 mmol, 1 equiv) in DMF (100 ml_) at room temperature was added anhydrous potassium carbonate (24.15 g, 175.01 mmol, 1 .5 equiv) portionwise. After stirring for 2 minutes, methyl-2-bromoacetate (13.3 ml_, 140.01 mmol, 1 .2 equiv) was added. The reaction mixture was heated at 80 °C for 4 h. After consumption of the starting material (TLC, 5 percent EtOAc in hexane), the reaction mixture was cooled to room temperature, diluted with water (100 ml_) and extracted with EtOAc (2 x 100 ml_). The combined organic layer was washed with brine solution (50 ml_), dried over anhydrous sodium sulphate, filtered and concentrated en vacuo to give the crude product. The crude product was purified by flash column chromatography (Combiflash) using a silica gel column and the product was eluted at 15percent ethyl acetate in hexane. Fractions containing product were concentrated to give methyl 2-(4- chlorophenoxy)acetate (22.5 g, 96.5percent yield) as pale yellow liquid. 1H NMR (400 MHz, CDC ): δ ppm 3.67 (s, 3 H), 4.78 (s, 2 H), 6.91 - 6.95 (m, 2 H), 7.28 - 7.32 (m, 2 H).
96.5%
Stage #1: With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 0.03 h;
Stage #2: at 80℃; for 4.00 h;
To a solution of 4-chlorophenol (15 g, 1 16.67 mmol, 1 equiv) in DMF (100 mL) at room temperature was added anhydrous potassium carbonate (24.15 g, 175.01 mmol, 1 .5 equiv ) portionwise. After stirring for 2 minutes, methyl-2-bromoacetate (13.3 mL, 140.01 mmol, 1 .2 equiv) was added. The reaction mixture was heated at 80 °C for 4 h. After consumption of the starting material (TLC, 5 percent EtOAc in hexane), the reaction mixture was cooled to room temperature, diluted with water (100 mL) and extracted with EtOAc (2 x 100 mL). The combined organic layer was washed with brine solution (50 mL), dried over anhydrous sodium sulphate, filtered and concentrated en vacuo to give the crude product. The crude product was purified by flash column chromatography (Combiflash) using a silica gel column and the product was eluted at 15percent ethyl acetate in hexane. Fractions containing product were concentrated to give methyl 2-(4-chlorophenoxy)acetate (22.5 g, 96.5percent yield) as pale yellow liquid. NMR (400 MHz, CDCI3): δ ppm 3.67 (s, 3 H), 4.78 (s, 2 H), 6.91 - 6.95 (m, 2 H), 7.28 - 7.32 (m, 2 H).
90% With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 24.00 h; General procedure: To a stirred solution of phenol (1 mmol) in DMF (3 mL) were added methyl bromoacetate (0.1 mL, 1 mmol) and K2CO3 (207 mg, 1.5 mmol), and the resulting mixture was heated at 80 °C for 24 h. After cooling, the reaction mixture was diluted with EtOAc, and filtered by celite pad. The filtrate was evaporated, and the residue was chromatographed on silica gel (15 g, hexane : acetone = 50 : 1 ~ 40 : 1) to give corresponding ether.
Reference: [1] Patent: WO2017/212423, 2017, A1. Location in patent: Page/Page column 71; 72
[2] Patent: WO2017/212425, 2017, A1. Location in patent: Page/Page column 68-69
[3] Bioorganic and Medicinal Chemistry Letters, 2014, vol. 24, # 16, p. 3732 - 3735
[4] Chemistry - A European Journal, 2017, vol. 23, # 50, p. 12096 - 12099
[5] Chemistry - A European Journal, 2014, vol. 20, # 18, p. 5492 - 5500
  • 2
  • [ 96-34-4 ]
  • [ 106-48-9 ]
  • [ 4841-22-9 ]
Reference: [1] Synthetic Communications, 2005, vol. 35, # 13, p. 1759 - 1764
[2] Synthetic Communications, 1984, vol. 14, # 1, p. 69 - 76
[3] Journal of Chemical Research, 2005, # 7, p. 432 - 433
[4] Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2006, vol. 45, # 5, p. 1312 - 1314
[5] Journal of Chemical Research, 2010, # 8, p. 452 - 454
[6] Journal of the Chemical Society of Pakistan, 2016, vol. 38, # 5, p. 974 - 980
[7] Molecules, 2017, vol. 22, # 1,
  • 3
  • [ 67-56-1 ]
  • [ 122-88-3 ]
  • [ 4841-22-9 ]
Reference: [1] Synthetic Communications, 2004, vol. 34, # 3, p. 377 - 382
[2] Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1981, vol. 20, # 7, p. 629 - 631
[3] Journal of the Indian Chemical Society, 1981, vol. 58, # 11, p. 1082 - 1083
[4] Journal of the Chemical Society, 1922, vol. 121, p. 1603
[5] Synthetic Communications, 2008, vol. 38, # 23, p. 4107 - 4115
  • 4
  • [ 67-56-1 ]
  • [ 51-68-3 ]
  • [ 4841-22-9 ]
Reference: [1] Chemical and Pharmaceutical Bulletin, 1980, vol. 28, # 3, p. 779 - 782
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