4-(3-CHLORO-PHENOXY)-BUTYRIC ACID synthesis

10synthesis methods

Product Name:4-(3-CHLORO-PHENOXY)-BUTYRIC ACID
CAS Number:5057-51-2
Molecular formula:C10H11ClO3
Molecular Weight:214.65

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108-43-0 Synthesis

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5057-51-2
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Yield:5057-51-2 47%

Reaction Conditions:

Stage #1: 4-butanolide;3-monochlorophenolwith sodium hydroxide at 170;
Stage #2: with hydrogenchloride in water;Cooling with ice bath;

Steps:

1.5a

1.5a Preparation of the 4-(3-chlorophenoxy)butyric acid 1 eq of NaOH (flakes) was dispersed in 1 eq of 3-chlorophenol 4and the thus obtained dispersion heated to 170° C. up to complete solubilization of the base. 1.4 eq of γ-butyrolactone were dropwise added to the solution, and the reaction mixture maintained at 170° C. for 5 hours. The reaction mixture was then poured into ice and then acidified with HCl 6N. The reaction product was extracted with CHCl₃, dehydrated with Na₂SO₄ and concentrated under vacuum. The obtained residue was purified by flash chromatography (oil ligroin/ethyl acetate 4:1 volume/volume). The acid 4-(3-chloro phenoxy)butyric (yellow solid) was obtained with a 47% yield. R_f=0.15 (oil ligroin/ethyl acetate 4:1); m.p. 47° C.; IR (nujol) (λ=cm^-1) 3223 (OH), 1709 (CO); ¹H-NMR (CDCl₃) δ 2.11 (qu, 2H, J=6.8 Hz), 2.58, (t, 2H, J=7.4 Hz), 4.0 (t, 2H, J=5.6 Hz), 6.76 (d, 1H, J=8.2 Hz), 6.88 (s, 1H), 6.92 (d, 1H, J=9.2 Hz), 7.18 (t, 1H, J=7.8 Hz); Anal. Calc. for C₁₀H₁₁ClO₃: C, 55.98; H, 5.17; Cl, 16.51. Found: C, 55.84; H, 5.16; Cl, 16.50.