Basic hydrolysis of cinnamyl chloride

Abstract

Basic hydrolysis of 3-chloro-1-phenyl-1-propene (cinnamyl chloride) to 3-phenyl-2-propen-1-ol (cinnamyl alcohol) and 1-phenyl-2-propen-1-ol was studied. The effects of the base type, presence of triethylbenzylammonium chloride as a phase transfer catalyst, and temperature were examined.

Structure−Odor Relationships

“…Another group of esters for which detailed odor measurement data has been published is the acetates, propionates, and butyrates of a range of 1-( p -alkyl)phenylethanols . The odor profile of these esters was defined using a set of 57 odor descriptors.…”

“…Another group of esters for which detailed odor measurement data has been published is the acetates, propionates, and butyrates of a range of 1-(palkyl)phenylethanols. 165 The odor profile of these esters was defined using a set of 57 odor descriptors. It is interesting to note that despite the findings of Sell, 158,159 the odors of apples and pears were combined to produce one descriptor.…”

One-pot synthesis of ortho-hydroxycinnamate esters

“…Oxidization by oxygen with 10% platinum on carbon catalyst (or palladium) in aqueous NaOH yielded 60.5% of salicylaldehyde 3a (Scheme 1.16). 42,43 5-Fluorosalicylaldehyde (5c) has been prepared from 4-fluorophenol (4c) in four steps in order to make 5-fluorosalicylic acid, an important derivative that has anti-inflammatory and other biological activity. 44 The procedure started with reductive amination of 4c using HCHO-Me 2 NH to give the amino derivative 28a and bis-diamino derivative 28b as a 6:1 mixture, which was converted with excess Ac 2 O to the corresponding acetates 29a and 29b…”

“…The Fries reaction can also be performed photochemically and the rearrangement of a formyl group under such conditions has been observed. When 4-tert-butylphenyl formate (35) was irradiated for 39 hours in benzene, 5-tert butyl-2-hydroxybenzaldehyde (5h) could be isolated in 7% yield (Scheme 1.20 This method was used to develop a facile synthesis of combretastatins A-1 (42) and B-1 (43). The natural products were obtained by coupling MOM-protected iodomethoxycatechol 40 with 3,4,5-trimethoxyphenylacetylene (41) in a Sonogashira reaction followed by reduction (Scheme 1.22).…”

“…3,4,4a-tetrahydro-1H,6H-5,10b-ethanophenanthridine (cis-3a-aryloctahydroindole nucleus) skeleton characterizes the crinine sub-class of Amaryllidaceae alkaloids such as crinine (131), powelline (132), crinamidine (133), and undulatine (134)(Figure 2.2) 43. …”