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Journal of Fluorine Chemistry
Volumn 130, Issue 5, 2009, Pages 505-508
A TFAA-H3PO4-mediated direct, metal-free and high-speed synthesis of aryl carboxylate esters from phenols
Author keywords

Carboxylic acid; Naphthol; O acylation; Phenol; Phosphoric acid; Trifluoroacetic anhydride
Indexed keywords

EID: 65349114107     PISSN: 00221139     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jfluchem.2009.02.006     Document Type: Article
Times cited : (12)
References (38)
  • 36
    • 65349126633 scopus 로고    scopus 로고
    • Typical procedure for the synthesis of phenyl carboxylate esters (1a-e): a mixture of acid (3, 1.0 mole), phenol (2, 1.0 mole) and 85% orthophosphoric acid (0.1 mole) was stirred under a normal and open atmosphere. To this, TFAA (4.0 mole) was added dropwise and the resulting mixture was allowed to stir at room temperature according to the time indicated in Table 1. The progress of the reaction was monitored by TLC. After the disappearance of the starting compounds the reaction mixture was added to crushed ice (50 g), extracted with diethyl ether (3 × 30 mL), washed with 10% NaOH solution (25 mL) followed by water (2 × 25 mL), dried over anhydrous sodium sulphate and concentrated to afford the desired product.
    • Typical procedure for the synthesis of phenyl carboxylate esters (1a-e): a mixture of acid (3, 1.0 mole), phenol (2, 1.0 mole) and 85% orthophosphoric acid (0.1 mole) was stirred under a normal and open atmosphere. To this, TFAA (4.0 mole) was added dropwise and the resulting mixture was allowed to stir at room temperature according to the time indicated in Table 1. The progress of the reaction was monitored by TLC. After the disappearance of the starting compounds the reaction mixture was added to crushed ice (50 g), extracted with diethyl ether (3 × 30 mL), washed with 10% NaOH solution (25 mL) followed by water (2 × 25 mL), dried over anhydrous sodium sulphate and concentrated to afford the desired product.
  • 37
    • 58149183749 scopus 로고    scopus 로고
    • For a recent review of dehydrative condensation reactions, see:
    • For a recent review of dehydrative condensation reactions, see:. Ishihara K. Tetrahedron 65 (2009) 1085-1109
    • (2009) Tetrahedron , vol.65 , pp. 1085-1109
    • Ishihara, K.1
  • 38
    • 36749050839 scopus 로고    scopus 로고
    • For an example of esterification using carboxylic anhydrides under auxiliary base- and solvent-free conditions, see:
    • For an example of esterification using carboxylic anhydrides under auxiliary base- and solvent-free conditions, see:. Sakakura A., Kawajiri K., Ohkubo T., Kosugi Y., and Ishihara K. J. Am. Chem. Soc. 129 (2007) 14775-14779
    • (2007) J. Am. Chem. Soc. , vol.129 , pp. 14775-14779
    • Sakakura, A.1    Kawajiri, K.2    Ohkubo, T.3    Kosugi, Y.4    Ishihara, K.5

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.