Notes- Attempted Preparation of Benzpinacole Carbonate

Sarel, Shalom; Pohoryles, Leo A.; Ben-Shoshan, Raphael

doi:10.1021/jo01094a637

Cited by 4 publications

(5 citation statements)

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“…The starting cyclic carbonates were prepared by the alkali-catalyzed exchange reaction between diethyl carbonate (or an m-dioxanone) with a diol (284,285). Vinyl carbonate condensed with ammonia to form the carbamate of glycol aldehyde (IX) (110).…”

Section: VImentioning

confidence: 99%

Esters of Carbamic Acid

Adams¹,

Baron²

1965

Chem. Rev.

241

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Section: VImentioning

confidence: 99%

Esters of Carbamic Acid

Adams¹,

Baron²

1965

Chem. Rev.

241

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“…The presence of two alkyl substituents in the 0021-8561/86/1434-0475$01.50/0 © 1986 American Chemical Society 2-position (4) led to a significant increase in the phenolic release as compared to derivatives 3 and 5. Previous investigators (Sarel et al, 1959) examining the ester interchange of 1,3-propanediol derivatives with diethyl carbonate have found that alkyl substituents on the 1,3propanediol backbone resulted in an increase in the intramolecular cyclization while reducing intermolecular condensation as measured by the yield of cyclic and acyclic carbonates obtained. The course of the reaction, intramolecular or intermolecular nucleophilic substitution, can be postulated to have a similar effect on aryl hydroxyalkyl carbonates comparable to Sarel's ethyl hydroxyalkyl carbonates.…”

Section: Resultsmentioning

confidence: 99%

Aryl hydroxyalkyl carbonates as precursors of phenolic flavoring agents

Podraza¹

1986

J. Agric. Food Chem.

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A variety of aryl hydroxyalkyl carbonates (1-7) have been synthesized and thermolyzed in the neat state at 150 and 250 °C. The aryl hydroxyalkyl carbonates 9 and 10 derived from glycerol and 11 derived from ethylene glycol decomposed at room temperature. Alkyl substitution in the diol moiety of the 1-[ [(aryloxy)carbonyl] oxy] -3-propanol derivatives 4 and 5 enhanced the phenolic release as compared to the unsubstituted derivative 3. 2-[[(2-Methoxy-4-formylphenoxy)carbonyl]oxy]-4-pentanol (8) decomposed at room temperature while 2-[[(2-methoxyphenoxy)carbonyl]oxy]-4-pentanol (5) was stable, which was attributed to the effectiveness of the aryl moieties as leaving groups. Increasing the chain length between the hydroxyl group and carbonate moiety from three methylene units (3), to four (6), to five (7) decreased the phenolic release from 67% to 45% to 10%, respectively.Alkyl-and alkoxy-substituted phenols such as 2-methoxyphenol have desirable flavor properties. These compounds have been detected in a wide variety of food products and have been used as flavoring agents (Fenaroli, 1975). However, their use as flavoring agents can be limited by their low odor threshold and high volatility. As a consequence, a limitation on the amount of the flavoring agent that can be utilized as well as losses on storage result.To overcome these limitations, the use of a phenolic flavor precursor could be employed. The requirements of such a flavor precursor would include being nonvolatile, odorless, and stable in the product on storage. Then, when

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“…A solution of 500 mg (1.90 mmol) of meso-a,a'-dimethylhydrobenzoin ( 16) was heated under reflux with 10 mg (0.10 mmol) of sodium methoxide and 250 mg (2.10 mmol) of diethyl carbonate in 30 ml of anhydrous toluene for 2 hr following the method outlined by Sarel and co-workers. 15 The ethanol which is formed was distilled and collected. The toluene and excess diethyl carbonate were removed under reduced pressure, and the resulting residue was dissolved in methylene chloride and worked up in the manner previously described for lb.…”

Section: Methodsmentioning

confidence: 99%

“…( 13) N. Isaacs and D. Kirkpatrick, Tetrahedron Lett., 3869 (1972). (14) Edmondson26 proved the structure of the principal 1,4-dlchlorlde of 3b (15) by diimide reduction to d/-2,5-dichlorohexane. (15) G. E. Heasley, R. V. Hodges, and V. L. Heasley, J. Org.…”

Section: (1971)mentioning

confidence: 99%