[ CAS No. 54884-55-8 ]

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2D
Chemical Structure| 54884-55-8
Chemical Structure| 54884-55-8
Structure of 54884-55-8

Quality Control of [ 54884-55-8 ]

Purity: {[proInfo.showProBatch.pb_purity]}

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SDS

Product Details of [ 54884-55-8 ]

CAS No. :54884-55-8MDL No. :MFCD08235006
Formula :C9H10O2Boiling Point :256.3°C at 760 mmHg
Linear Structure Formula :-InChI Key :-
M.W :150.17Pubchem ID :640238
Synonyms :

Computed Properties of [ 54884-55-8 ]

TPSA : 26.3 H-Bond Acceptor Count : 2
XLogP3 : 1.7 H-Bond Donor Count : 0
SP3 : 0.22 Rotatable Bond Count : 2

Safety of [ 54884-55-8 ]

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 [ 54884-55-8 ]

  • Upstream synthesis route of [ 54884-55-8 ]
  • Downstream synthetic route of [ 54884-55-8 ]

[ 54884-55-8 ] Synthesis Path-Upstream   1~10

  • 1
  • [ 18362-36-2 ]
  • [ 74-88-4 ]
  • [ 54884-55-8 ]
YieldReaction ConditionsOperation in experiment
72%
Stage #1: With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 0.50 h;
Stage #2: at 20℃;
General procedure: To a solution of the hydroxy-methylbenzaldehyde (34 mg,0.25 mmol) in anhydrous DMF (6.0 mL), K2CO3 (35 mg,0.25 mmol) was added and the mixture was stirred at room temperaturefor 30 minutes. Then, methyl iodide (30 μL, 68 mg,0.5 mmol) was added and the reaction was stirred at room temperatureovernight. The reaction was quenched by the additionof distilled water, and the aqueous phase was extracted threetimes with ethyl acetate. The combined organic phases weredried with MgSO4 and concentrated in vacuo. The residue waspurified by column chromatography on silica gel.
Reference: [1] Tetrahedron, 2008, vol. 64, # 49, p. 11050 - 11057
[2] Beilstein Journal of Organic Chemistry, 2018, vol. 14, p. 734 - 746
[3] Journal of the American Chemical Society, 1979, vol. 101, p. 7114 - 7116
  • 2
  • [ 2944-49-2 ]
  • [ 54884-55-8 ]
YieldReaction ConditionsOperation in experiment
44.2% With dipotassium peroxodisulfate; copper(ll) sulfate pentahydrate In water; acetonitrile for 0.25 h; Reflux 2-Methoxy-6-methylbenzaldehyde
Potassium peroxy disulphate (89.31g, 0.33mol) and copper (II) sulphate pentahydrate (27.22 g, 0.11 mol) was added to a solution of 2,3-dimethylanisole (15 g, 0.11 mol) in acetonitrile water mixture (750 ml, 1:1).
The reaction mixture was stirred for 15 min at reflux until no starting material remained as judged by TLC (Thin Layer Chromatography).
On cooling the reaction mixture to room temperature, the product was extracted into dichloromethane (2 x 225ml).
The organic layer was washed with water (2 x 100ml) and brine solution (100 ml).
The organic layer was dried over sodium sulfate and concentrated under reduced pressure to give the crude product.
Column chromatography using 4/96 ethyl acetate/ hexane yielded 2-Methoxy-6-methylbenzaldehyde (7.32g, 44.2percent).
1H NMR (300 MHz, CDCl3), δ 2.60 (3H, s), 3.90 (3H, s), 6.80(2H, t), 7.40(1H, t), 10.65(1 H, s).
Reference: [1] Tetrahedron, 1996, vol. 52, # 6, p. 2199 - 2216
[2] Chemical Communications, 2013, vol. 49, # 77, p. 8626 - 8628
[3] Angewandte Chemie - International Edition, 2013, vol. 52, # 2, p. 762 - 766[4] Angew. Chem., 2013, vol. 125, # 2, p. 791 - 796,6
[5] Chemistry - A European Journal, 2015, vol. 21, # 29, p. 10322 - 10325
[6] Patent: EP2110374, 2009, A1. Location in patent: Page/Page column 26-27
[7] Synthesis, 1983, # 12, p. 1000 - 1002
[8] Synthesis, 1987, # 8, p. 723 - 724
[9] Synthesis, 1984, # 6, p. 504 - 506
[10] European Journal of Organic Chemistry, 2010, # 3, p. 555 - 564
[11] Angewandte Chemie - International Edition, 2012, vol. 51, # 4, p. 1071 - 1074
[12] Patent: WO2015/153410, 2015, A1. Location in patent: Paragraph 00207-00211
[13] Chemical Communications, 2016, vol. 52, # 60, p. 9426 - 9429
[14] Patent: WO2018/17858, 2018, A1. Location in patent: Paragraph 0157-0158
[15] Chemistry - A European Journal, 2018, vol. 24, # 14, p. 3413 - 3419
  • 3
  • [ 89244-39-3 ]
  • [ 54884-55-8 ]
Reference: [1] Chemical and pharmaceutical bulletin, 2002, vol. 50, # 10, p. 1358 - 1361
[2] Journal of Labelled Compounds and Radiopharmaceuticals, 1995, vol. 36, # 12, p. 1183 - 1191
[3] Patent: WO2015/66241, 2015, A1. Location in patent: Page/Page column 48
  • 4
  • [ 35387-94-1 ]
  • [ 68-12-2 ]
  • [ 54884-55-8 ]
Reference: [1] Organic Letters, 2010, vol. 12, # 8, p. 1732 - 1735
  • 5
  • [ 89244-40-6 ]
  • [ 54884-55-8 ]
Reference: [1] Synthesis, 1984, # 6, p. 504 - 506
[2] European Journal of Organic Chemistry, 2010, # 3, p. 555 - 564
  • 6
  • [ 2944-49-2 ]
  • [ 54884-55-8 ]
  • [ 137644-93-0 ]
Reference: [1] European Journal of Organic Chemistry, 2010, # 3, p. 555 - 564
  • 7
  • [ 6520-83-8 ]
  • [ 54884-55-8 ]
Reference: [1] Chemical and pharmaceutical bulletin, 2002, vol. 50, # 10, p. 1358 - 1361
  • 8
  • [ 526-75-0 ]
  • [ 54884-55-8 ]
Reference: [1] Chemistry - A European Journal, 2015, vol. 21, # 29, p. 10322 - 10325
  • 9
  • [ 20383-28-2 ]
  • [ 54884-55-8 ]
Reference: [1] Journal of Organic Chemistry, 2018, vol. 83, # 4, p. 1687 - 1700
  • 10
  • [ 3724-55-8 ]
  • [ 66947-61-3 ]
  • [ 54884-55-8 ]
Reference: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1981, p. 1383 - 1385
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