ChemicalBook CAS DataBase List 2-(3-METHYLPHENOXY)ETHANOL

2-(3-METHYLPHENOXY)ETHANOL synthesis

6synthesis methods

Product Name:2-(3-METHYLPHENOXY)ETHANOL
CAS Number:13605-19-1
Molecular formula:C9H12O2
Molecular Weight:152.19

108-39-4
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13605-19-1
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Yield:-

Reaction Conditions:

with potassium carbonate in N,N-dimethyl-formamide at 120;

Steps:

Type A (step i)
General procedure: To a mixtureof 3-chlorophenol or 3-methylphenol (1.0 equiv.) and K₂CO₃(1.5 equiv.) in DMF was added bromoethanol (1.5 equiv.) and stirred at 120 ^oC. After the reaction wascompleted, the mixture was added to water, extracted with EtOAc, dried andconcentrated under reduced pressure for further column chromatography. Theresidue was purified by silica gel column chromatography (n-hexane : EtOAc = 2:1) to afford 3-substitutedphenol. 3-m-Tolyloxyethanol (14a): Pale yellow liquid; ¹HNMR (400 MHz, CDCl₃) δ 7.16 (1H, t, J = 8.0 Hz), 6.71-6.79 (3H, m),4.05 (2H, dd, J = 4.8, 4.0 Hz), 3.93 (2H, br s), 2.43 (OH, br s),2.32 (3H, s); ¹³C NMR (100 MHz, CDCl₃) δ 158.6,139.6, 129.3, 121.9, 115.4, 111.4, 69.0, 61.5, 21.5; IR (neat, cm^-1)3366, 2925, 2872, 1603, 1575, 1491, 1264, 1159, 1081, 1054.

References:

Gim, Hyo Jin;Li, Hua;Jeong, Ji Hye;Lee, Su Jeong;Sung, Mi-Kyung;Song, Mi-Young;Park, Byung-Hyun;Oh, Soo Jin;Ryu, Jae-Ha;Jeon, Raok [Bioorganic and Medicinal Chemistry,2015,vol. 23,# 13,art. no. 12258,p. 3322 - 3336] Location in patent:supporting information