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Chemical Structure| 90296-27-8 Chemical Structure| 90296-27-8

Structure of 90296-27-8

Chemical Structure| 90296-27-8

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Product Details of [ 90296-27-8 ]

CAS No. :90296-27-8
Formula : C8H9ClO2
M.W : 172.61
SMILES Code : OCC1=CC=C(Cl)C=C1OC
MDL No. :MFCD02683547
InChI Key :AXXPZAITCCIOIA-UHFFFAOYSA-N
Pubchem ID :3549393

Safety of [ 90296-27-8 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302
Precautionary Statements:P264-P270-P301+P312-P330-P501

Application In Synthesis of [ 90296-27-8 ]

* 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 [ 90296-27-8 ]

[ 90296-27-8 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 78955-90-5 ]
  • [ 90296-27-8 ]
YieldReaction ConditionsOperation in experiment
87% With lithium aluminium tetrahydride; In tetrahydrofuran; at 0 - 20℃; for 3h;Inert atmosphere; To a solution under nitrogen gas of methyl 2-methoxy-4-chlorobenzoate (10.0 g, 50 mmol) in THF (100 mL) was added at 0C a 1.0 M LiAlH4 solution in THF (75 mL, 75 mmol). The resulting reaction mixture was stirred at room temperature for 3 hours. Then, the solvent was removed under vacuum and the residue was stirred in a 5% aqueous acetic acid solution (pH 6) for 15 minutes. The aqueous layer was extracted with EtOAc, then the combined organic layers were washed with brine, dried over Na2SO4, filtered, and concentrated under reduced pressure to give the crude product as a tan oil. The crude product was purified by flash chromatography (gradient petroleum ether/EtOAc 100/5) to give 7.5 g (yield = 87 %) of white solid corresponding to 2-methoxy-4-chlorobenzyl alcohol (14-1). 1H NMR (400 MHz, CDCl3)
With lithium borohydride; In tetrahydrofuran; at 60℃; for 16h;Inert atmosphere; General procedure: To a solution of methyl 4-bromo-2-methoxybenzoate (7.14g, 29mmol) in THF (35mL) was added a 2M solution of LiBH4 in THF (35mL, 70mmol, 2.4equiv). The solution was heated at 60C for 16h. The reaction was then cooled to room temperature, and the solvent was removed under vacuum. The residue was stirred in a 5% aqueous acetic acid solution (pH 6) for 15min. The aqueous layer was extracted with EtOAc (2×50mL), then the combined organic extracts were washed with brine, dried (MgSO4), filtered, and concentrated to yield the crude product as a tan oil. The oil was purified by flash chromatography using 5% EtOAc in hexanes to provide 5.96g (94%) of the product as a white solid.
With methanol; sodium tetrahydroborate; at 60℃; for 4h; Step 2; To the solution of meihyl 4-chioro-2-methoxybenzoate in 5 mL of MeOH was added aBH4 (304 mg, 8.04 mmol). The reaction was stirred at 60 C for 4h. The completion of the reaction was monitored by HPLC. Upon completion, solvent was removed in vacuo, H2O was added to the crude residue and the reaction mixture was extracted with EtOAc. The combined organic layers were washed with saturated aqueous NaHC03, brine and dried over Na2'04. Filtration and removal of the solvent provided 49 mg (35% overall yield) of the title compound as a colorless oil, which was used without further purification; . 1H N (400 MHz, CDC ) ~ 7.22 (d, J - 7.9 Hz, 1 H), 6.94 (dd, J = 2,0, 7.9 Hz, 1 H), 6.88 (d, J ~ 2.0 Hz, 1 H), 4.65 (s, 2 H), 3.87 (s, 3 H).
YieldReaction ConditionsOperation in experiment
100% (137-2) Under nitrogen atmosphere, a solution of the compound of Example 137-1 (4.50 g) in THF (75 mL) was cooled to 0C, and thereto was added LiAlH4 (984 mg) in portions. The mixture was stirred at room temperature for 2 hours, and cooled to 0C. Water (1.0 mL), a 2N aqueous NaOH solution (2.0 mL) and water (1.0 mL) were added successively to the mixture, and the mixture was stirred at room temperature for 1 hour. The solid was collected by filtration, and washed with ethyl acetate. The filtrate and the washing were combined, washed with a saturated brine, and dried over MgSO4. The solvent was evaporated under reduced pressure to give (4-chloro-2-methoxyphenyl)methanol (3.88 g, 100 %). 1H NMR (CDCl3, 400MHz) δ 7.21(d, 1H, J=8.0 Hz), 6.93 (dd, 1H, J=1.9, 8.0 Hz), 6.87 (d, 1H, J=1.9Hz), 4.64 (s, 2H), 3.86 (s, 3H).
 

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