Solid-supported acids for debenzylation of aryl benzyl ethers

Journal of Organic Chemistry

Volumn 71, Issue 7, 2006, Pages 2892-2895

  Petchmanee, Thaninee ^a   Ploypradith, Poonsakdi ^a   Ruchirawat, Somsak ^a,b  

^a Toxicology and Management of Chemicals   (Thailand)

^b MAHIDOL UNIVERSITY   (Thailand)

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC DEBENZYLATION PRODUCTS; DEBENZYLATION; SOLID-SUPPORTED ACIDS;

AROMATIC COMPOUNDS; BENZENE; ETHERS; METHANOL; STOICHIOMETRY;

ORGANIC ACIDS;

AROMATIC COMPOUND; BENZYL DERIVATIVE; ESTER DERIVATIVE; METHANOL; STYRENE DERIVATIVE;

ARTICLE; DEBENZYLATION; HYDROGENATION; PHASE TRANSITION; PRODUCTIVITY; REACTION ANALYSIS; RECYCLING; REDUCTION; STOICHIOMETRY;

ALLYL COMPOUNDS; BENZYL COMPOUNDS; COMBINATORIAL CHEMISTRY TECHNIQUES; ESTERS; INDICATORS AND REAGENTS; MOLECULAR STRUCTURE; RESINS, SYNTHETIC; SOLVENTS; STEREOISOMERISM; TEMPERATURE;

EID: 33645515693     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo052337v     Document Type: Article

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43. A number of other reaction conditions employing 1.1-3.0 equiv of Amberlyst-15 in toluene at 110 °C for 3-6 h gave 9 together with some detectable amount of 10. When 5 equiv was used and the reaction time was less than 6 h, the reaction did not proceed to completion and the formation of 10 was observed. Interestingly, p-TsOH (1.5 equiv) under similar reaction conditions for 3 h effectively cleaved the PMB ether and only a trace amount of 10 was observed in the crude mixture.
44. 1H NMR. Piperonal was used as an internal standard, and the amount of the remaining starting material was determined by relative integration.
45. Approximately 83% of benzyl ether was consumed.
46. After some experimentation, we found that ONB and PNB ethers were effectively cleaved by potassium tert-butoxide in refluxing tert-butyl alcohol. Vanillin was obtained in 84% and 80% yields from 15 and 16, respectively. See Supporting Information for details.
47. Without methanol, the reaction gave 8 in 57% yield as well as 17 and 18 in 12% combined yield.
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52. For complete characterization of compound 10 and 11, please see the Supporting Information.