1-Propanone, 1-(3-chloro-4-hydroxyphenyl)- synthesis

8synthesis methods

Product Name:1-Propanone, 1-(3-chloro-4-hydroxyphenyl)-
CAS Number:2892-27-5
Molecular formula:C9H9ClO2
Molecular Weight:184.62

Preparation by Fries rearrangement of o-chlorophenyl propio nate with aluminium chloride, at 165° for 1 h (98%) or at 110° for 2 h (63%)
Preparation by demethylation of 3-chloro-4-methoxy-propiophenone (m.p. 88°) (m.p. 89–90°) with refluxing pyridinium chloride for 15 min (75%)
Preparation by diazotization of 3-amino-4-hydroxypropiophenone, followed by decomposition of the diazonium salt obtained (52%)
Preparation by chlorination of p-hydroxypropiophenone with chlorine in cooled acetic acid (57%).

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1-Propanone, 1-(3-chloro-4-hydroxyphenyl)-

2892-27-5
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Yield:2892-27-5 48.4%

Reaction Conditions:

aluminium chloride in hexane;ethyl acetate;

Steps:

I.B B.

B. 3-chloro-4-hydroxpropiophenone STR23 To anhydrous aluminium chloride (37 g, 0.27 mole), o-chlorophenyl propionate (24.8 g, 0.13 mole) was added rapidly (vigorous reaction). The reaction mixture was heated at 120°-130° C. (in a metal bath) for 30-45 min. After cooling, the aluminum chloride reaction mixture was decomposed with a mixture of ice and concentrated HCl. The solid organic material was filtered off by suction, and was washed with much cold water giving 18-20 g of solids. This product was recrystallized several times from ethyl acetate-hexane giving two parts: (1) 13-14 g insoluble in hexane and (2) 5-6 g from evaporation of the ethyl acetate-hexane filtrates. The 13-14 g of hexane insoluble material was recrystallized several times from mixtures of ethyl acetate and hexane. It was charcoaled while in the hot ethyl acetate solution and gave finally 3-chloro-4-hydroxypropiophenone (12 g, 48.4%) mp 114°-115° C. (D. Chakravarti and B. Majurndar., J. Indian Chem. Soc., 16, 151-159 (1939) reported a mp of 80° C. for this product) Anal for C₉ H₉ O₂ Cl M.W. 184.63 Calcd: C, 58.54; H 4.91 Found: C, 58.41; H 4.76.

References:

US4347176,1982,A

766-51-8 Synthesis