Anisaldehyde alcohol

Colour Reactions. Rochelmeyer (1939) has provided a list of colour reactions given by solasodine and solasodiene (solanosodine), with reagents usually applied to the sterols, and Briggs et al. have found that when concentrated sulphuric acid (1 mil) is carefully added to a solution of solasonine or solasodine in hot alcohol (1 mil) a characteristic, intense, greenish-yellow fluorescence is produced, a reaction which is not given by solanine or solanidine. They have also found that intense colours are formed when solasonine or solasodine is mixed with resorcinol, or one of a variety of aldehydes, and boiled with concentrated hydrochloric acid. Colours are also produced with this test by cholesterol, digitonin, jacobine carbazole, pyrrole, or nicotine, the most intense colours being formed with p-hydroxybenzaldehyde or anisaldehyde. 

In order to overcome these two issues, we reversed the order of the reaction sequence, as summarized in Scheme 1.20. We took advantage of the alcohol functional group in 50. Oxidation ofpMB of 50 with DDQ proceeded smoothly to form cyclic aminal 52 (as a mixture of a and P = 11.5 1) in toluene at 0-10 °C. The resulting DDQH, which is insoluble in toluene, was filtered off, and isolated DDQH could be recycled as we demonstrated in the Proscar process (see p. 92) [32]. Thus, this process minimizes the impact to the environment from an oxidizing reagent. Cyclic aminal 52 was solvolyzed with NaOH in MeOH at 40 °C. The resulted anisaldehyde was reduced in situ to pMBOH 43 by addition of NaBH4 and the desired amino alcohol 53 was isolated by direct crystallization from the reaction mixture, upon neutralization with acetic acid, in 94% yield and >99.9% ee after crystallization from toluene-heptane. 

Fluoride ion is effective in promoting the reduction of aldehydes by organosil-icon hydrides (Eq. 161). The source of fluoride ion is important to the efficiency of reduction. Triethylsilane reduces benzaldehyde to triethylbenzyloxysilane in 36% yield within 10-12 hours in anhydrous acetonitrile solvent at room temperature when tetraethylammonium fluoride (TEAF) is used as the fluoride ion source and in 96% yield when cesium fluoride is used.83 The carbonyl functions of both p-anisaldehyde and cinnamaldehyde are reduced under similar conditions. Potassium bromide or chloride, or tetramethylammonium bromide or chloride are not effective at promoting similar behavior under these reaction conditions.83 Moderate yields of alcohols are obtained by the KF-catalyzed PMHS, (EtO SiH, or Me(EtO)2SiH reduction of aldehydes.80,83,79... 

Anisyl Alcohol (/imoles) Veratryl Alcohol (/imoles) % yield of Anisaldehyde % TDCSPPFeCl Left After Reaction... 

Typical examples are listed in Table 2.1. A few oxidations are effected by RuO but in general it is too powerful an oxidant for this purpose. The system RuCyaq. NaCl-CCy Pt anode oxidised benzyl alcohol to benzaldehyde and benzoic acid and p-anisaldehyde to p-anisic acid [24], and a wide range of primary alcohols and aldehydes were converted to carboxylic acids, secondary alcohols to ketones, l, -diols to lactones and keto acids from RuOj/aq. NaCl pH 4/Na(H3PO )/Pt electrodes (Tables 2.1-2.4). The system [RuO ] "/aq. K3(S303)/Adogen /CH3Cl3 oxidised benzyhc alcohols to aldehydes [30]. The oxidation catalyst TPAP (( Pr N)[RuO ]) (cf. 1.3.4) is extremely useful as an oxidant of primary alcohols to aldehydes and secondary alcohols to ketones without... 

Uses. Anethole is used in large quantities in the alcoholic beverage industry (Pernod, Ouzo) and in oral hygiene products. Some crude anethole is converted into anisaldehyde. 

Pure anise alcohol for perfumery and flavor purposes is prepared by hydrogenation of anisaldehyde. It is used in perfumery in blossom compositions (e.g., lilac and gardenia types) and in flavors for confectionery and beverages. 

Other industrial processes are the liquid-phase oxidation in the presence of cobalt catalysts [171] and the electrochemical oxidation in the presence of lower aliphatic alcohols via the corresponding anisaldehyde dialkyl acetal [172]. 

Addition of (C2Hs)2Zn to RCHO.1 The diol 1, prepared by Barbier addition of CsHjMgBr (2 equiv.) to the acetonide of dimethyl (R,R)-tartrate,2 converts Ti(OC2H5)4 into the optically active spirotitanate 2. In the presence of 0.05-2.0 equiv. of 2, diethylzinc reacts with anisaldehyde in toluene at 0° to form the (R)-alcohol 3 (equation I). The enantioselectivity and the chemical yield increases with an increase in 2. Surprisingly, the enantioselectivity is reversed in reactions of the... 

Examples of this reaction have long been known, and several have been discussed above (pp. 99-102). Applications of the method to aldehydes of the aromatic series have been reported more recently. Nenitzescu and Gav t 89 observed that equimolal mixtures of benzalde-hyde or anisaldehyde with formaldehyde led to the formation of both possible acids and alcohols, and that if formaldehyde was present in large excess the aromatic- alcohol, and little of the corresponding acid, was formed. The procedure may therefore be looked upon as a method for reducing aromatic aldehydes. Davidson and Bogert90 have worked out experimental conditions for carrying out the reduction of aldehydes by this means to give 85-90% yields of the alcohols. 

Lund 12°) was first in applying cpe in the oxidation of a primary alcohol to an aldehyde (which under constant current conditions would be partly or completely oxidized to the corresponding carboxylic acid) 121 Anisyl alcohol displays two anodic waves in acetonitrile-sodium perchlorate withiTj /2 of 1.22 and 1.64 V vs. Ag/0.1 M Ag Cpe at the plateau of the first wave (1.35 V) in the same medium consumed only 5 % of the theoretically calculated amount of electricity and no carbonyl compound was formed. Addition of a three-fold excess of pyridine (to act as a proton acceptor) gave a 72 % of anisaldehyde ... 

Complicated mixtures may sometimes take on an identity which is no more difficult to recognize than a single chemical. Perfumes such as Anais Anais or Giorgio are as instantly recognizable as phenylethyl alcohol or anisaldehyde. Similarly lavender oil or geranium have a unique and memorable identity. Indeed, in our experience, students often can more easily identify these complicated mixtures than single chemical materials. Just why some perfumes have such strong identity is not fully understood, but, as will be discussed later, much of the skill of the perfumer lies in the ability to achieve such an identity in a composition. 

Amyl cinnamic aldehyde Amyl salicylate Anisaldehyde Aurantiol Benzaldehyde Benzyl acetate Benzyl salicylate Brahmanol Cal one Cashmeran Cedramber Cedryl acetate Cinnamic alcohol Citral Citronellal Citronellol Citronellyl acetate Coumarin... 

FIGURE 4-8. Comparison of optimized separation on phenyl and cyano (CN) phases compared to a C18 phase. Columns 8 mm ID x 10 cm Radial Pak cartridges containing Nova-Pak bonded phase, (a) Nova-Pak C18 using a mobile phase of acetonitrile water (35 65), and Nova-Pak phenyl using a mobile phase of methanol ace-tonitrile water (33 8 59). (b) Nova-Pak C18 using a mobile phase the same as in a and Nova-Pak CN using a mobile phase of tetrahydrofuran water (10 90). Flow rate 2 mL/min. Detection 254 nm. Sample 1. benzyl alcohol 2. 2-phenoxyethanol 3. anisaldehyde 4. acetophenone 5. p-tolualdehyde 6. p-methylacetophenone, 7. anis-ole 8. phenetole. 

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