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[ CAS No. 129716-11-6 ] {[proInfo.proName]}

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Chemical Structure| 129716-11-6
Chemical Structure| 129716-11-6
Structure of 129716-11-6 * Storage: {[proInfo.prStorage]}
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Product Details of [ 129716-11-6 ]

CAS No. :129716-11-6 MDL No. :MFCD06201140
Formula : C8H9ClO Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 156.61 Pubchem ID :-
Synonyms :

Safety of [ 129716-11-6 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P264-P280-P302+P352+P332+P313+P362+P364-P305+P351+P338+P337+P313 UN#:N/A
Hazard Statements:H315-H319 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 129716-11-6 ]

* 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 [ 129716-11-6 ]

[ 129716-11-6 ] Synthesis Path-Downstream   1~5

  • 1
  • [ 15393-58-5 ]
  • [ 129716-11-6 ]
YieldReaction ConditionsOperation in experiment
97% With lithium aluminium tetrahydride In tetrahydrofuran 11 A sample of 4-chloro-2-methylbenzoic acid was converted to the ethyl ester using ethanol/triethyl orthoformate/sulfuric acid in >95% yield. Reduction of the ester with LiAlH4/tetrahydrofuran gave 4-chloro-2-methylbenzyl alcohol in 97% yield as a colorless oil. Subsequent treatment with thionyl chloride/pyridine/CH2Cl2 gave the substituted benzyl chloride. The latter, on treatment with 40% excess sodium cyanide in DMF at 90° C. for 20 min. and normal work-up and crystallization from hexane/butyl chloride (2 crops) gave 4-chloro-2-methylbenzyl cyanide in 80% overall yield.This latter compound on treatment with formaldehyde in the presence of DBU was found to quickly form an equilibrium at relatively low conversion to the desired alcohol which was then slowly dehydrated to an atroponitrile. Consequently, a mixture of the nitrile (688 mg, 4.15 mmol) and formaldehyde in THF (2.75 mL) was treated with DBU (55 μL), then quenched at 7 min with 3N HCl. Work-up recovered starting material (528 mg) by crystallization from butyl chloride/hexane. Two cycles of retreatment followed by flash chromatography (5% 90% ethyl acetate in hexane) recovered 313 mg of the desired alcohol as a pale yellow oil. TLC: Rf 0.13 (silica gel, ethyl acetate:hexane=1:4)
With lithium aluminium tetrahydride In tetrahydrofuran
With lithium aluminium tetrahydride In tetrahydrofuran for 1h; Reflux; The 4-chloro-2-methyl-benzyl chloride is readily synthesized according to the following scheme from T. S Osdene and et al, Journal of Medicinal Chemistry., 10, 431-434 (1967).
With lithium aluminium tetrahydride In tetrahydrofuran for 1h; Heating / reflux;

  • 2
  • [ 615-60-1 ]
  • [ 58966-29-3 ]
  • [ 129716-11-6 ]
YieldReaction ConditionsOperation in experiment
With NADPH generating system; rat liver microsomes In water at 35 - 36℃; for 1h; or 4-tert-butyl-1,2-dimethylbenzene;
In water at 35 - 36℃; for 1h; rat liver microsomes, NADPH generating system, phosphate buffer; Yield given. Yields of byproduct given. Title compound not separated from byproducts;
With ammonium cerium(IV) nitrate; sulfuric acid; water 1.) AcOH, 60 deg C, 28 h; Multistep reaction;
  • 3
  • [ 7499-07-2 ]
  • [ 129716-11-6 ]
YieldReaction ConditionsOperation in experiment
100% With lithium aluminium tetrahydride In tetrahydrofuran at 20℃; for 2h; 75.1 A mixture containing 4-Chloro-2-methyl-benzoic acid (4g, 23 mmol) and LiAlH4 (890 mg, 23.5 mmol) in 250 mL of THF under a nitrogen atmosphere was allowed to stir at room temperature for 2 hours. The reaction was quenched with sodium sulfate decahydrate. The mixture was filtered through a pad of Celite and the filter cake washed with THF. The filtrate was concentrated under reduced pressure. Purification of the residue via biotage eluting with 30% ethyl acetate/hexanes gave (4-Chloro-2-methyl-phenyl)-methanol (3.70 g, 100%) as a colorless oil. 1H NMR (CDC13, 400 MHz) 6 7. 30-7. 25 (1H, m), 7.18-7. 14 (2H, m), 4.66 (2H, d, J5. 8 Hz), 2.32 (3H, s.)
With diborane In tetrahydrofuran at 0℃; for 1.5h;
Multi-step reaction with 2 steps 1: ethanol / sulfuric acid 2: lithium aluminium tetrahydride / tetrahydrofuran
  • 5
  • [ 129716-11-6 ]
  • [ 7499-07-2 ]
YieldReaction ConditionsOperation in experiment
68% With dichloro(1,5-cyclooctadiene)ruthenium(II); C30H30N3P2(1+)*Cl(1-); potassium hydroxide In toluene at 120℃; for 24h; Inert atmosphere; Schlenk technique;
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