(4-Chloro-3-Methoxyphenyl)Methanol

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CAS:13726-17-5
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(4-Chloro-3-Methoxyphenyl)Methanol Basic information
Product Name:(4-Chloro-3-Methoxyphenyl)Methanol
Synonyms:(4-Chloro-3-Methoxyphenyl)Methanol;4-Chloro-3-methoxybenzyl alcohol;Benzenemethanol, 4-chloro-3-methoxy-
CAS:13726-17-5
MF:C8H9ClO2
MW:172.61
EINECS:
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Mol File:13726-17-5.mol
(4-Chloro-3-Methoxyphenyl)Methanol Structure
(4-Chloro-3-Methoxyphenyl)Methanol Chemical Properties
Boiling point 279.2±25.0 °C(Predicted)
density 1.239±0.06 g/cm3(Predicted)
storage temp. Sealed in dry,Room Temperature
pka14.04±0.10(Predicted)
AppearanceWhite to off-white Solid
Safety Information
HS Code 2909498090
MSDS Information
(4-Chloro-3-Methoxyphenyl)Methanol Usage And Synthesis
Synthesis Reference(s)Journal of Medicinal Chemistry, 32, p. 1757, 1989 DOI: 10.1021/jm00128a016
Synthesis
4-CHLORO-3-METHOXYBENZOIC ACID

85740-98-3

(4-Chloro-3-Methoxyphenyl)Methanol

13726-17-5

Step 1. Dissolve 4-chloro-3-methoxybenzoic acid (1.12 g, 5.98 mmol) in tetrahydrofuran (30 mL) under ice bath conditions with stirring. A tetrahydrofuran solution of 1.0 M lithium aluminum hydride (7.18 mL, 7.18 mmol) was slowly added over approximately 5 minutes. Ice bath conditions were maintained and stirring of the reaction mixture was continued for 2 hours. Upon completion of the reaction, the reaction was quenched by slow dropwise addition of water (0.27 mL), followed by addition of 15% aqueous sodium hydroxide solution (0.27 mL), and finally water (0.82 mL). The resulting suspension was filtered and the collected solid was washed with ethyl acetate. The filtrates were combined and concentrated under reduced pressure to give (4-chloro-3-methoxyphenyl)methanol as a colorless oil (737 mg, 71% yield). The product was characterized by 1H NMR (400 MHz, CDCl3): δ 3.92 (s, 3H), 4.67 (s, 2H), 6.87 (d, J = 7.6 Hz, 1H), 6.98 (s, 1H), 7.33 (d, J = 7.6 Hz, 1H).

References[1] Patent: US2002/77486, 2002, A1
[2] Patent: US6906063, 2005, B2
[3] Patent: EP2314593, 2016, B1. Location in patent: Paragraph 0201
[4] Journal of Medicinal Chemistry, 1987, vol. 30, # 10, p. 1887 - 1891
[5] Journal of Medicinal Chemistry, 1992, vol. 35, # 23, p. 4408 - 4414
(4-Chloro-3-Methoxyphenyl)Methanol Preparation Products And Raw materials
Raw materials3-CHLORO-4-METHOXYBENZALDEHYDE-->Water-->4-CHLORO-3-METHOXYBENZOIC ACID-->Lithium Aluminum Hydride-->Tetrahydrofuran-->Sodium hydroxide
Preparation Products1-Chloro-4-(chloromethyl)-2-methoxybenzene
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