Preparation of Cyclopropyl p-Hydroxyphenyl Ketone and Its Precursor 3-Chloropropyl p-Hydroxyphenyl Ketone
详细信息 查看全文
- 作者：Sou-Jen Chang ; Dilinie P. Fernando ; and Steve King
- 刊名：Organic Process Research & Development
- 出版年：2001
- 出版时间：March 2001
- 年：2001
- 卷：5
- 期：2
- 页码：141 - 143
- 全文大小：40K
- 年卷期：v.5,no.2(March 2001)
- ISSN：1520-586X
文摘
3-Hydroxypropyl p-hydroxyphenyl ketone (7) is selectivelyprepared in 96% yield by the Friedel-Crafts reaction of anisole,4-chlorobutyryl chloride (5) and aluminum chloride in chlorobenzene at 100 
C, followed by quenching the mixture in aqueous hydrochloride at <40 C. Heating of the quenched aqueousmixture to 100 C converts hydroxyl compound 7 cleanly to3-chloropropyl p-hydroxyphenyl ketone (2) in 95-99% yield.Compounds 2 and 7 are interchangeable. Heating chloride 2with aluminum chloride produces alcohol 7; whereas heating7 in aqueous hydrochloric acid gives 2 exclusively. The chloride2 is easily converted to cyclopropyl p-hydroxyphenyl ketone (1)at 0 C using 6 equiv of aqueous sodium hydroxide or 2 equivof potassium tert-butoxide in 92 and 96% yields, respectively.
C, followed by quenching the mixture in aqueous hydrochloride at <40 C. Heating of the quenched aqueousmixture to 100 C converts hydroxyl compound 7 cleanly to3-chloropropyl p-hydroxyphenyl ketone (2) in 95-99% yield.Compounds 2 and 7 are interchangeable. Heating chloride 2with aluminum chloride produces alcohol 7; whereas heating7 in aqueous hydrochloric acid gives 2 exclusively. The chloride2 is easily converted to cyclopropyl p-hydroxyphenyl ketone (1)at 0 C using 6 equiv of aqueous sodium hydroxide or 2 equivof potassium tert-butoxide in 92 and 96% yields, respectively.