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Volumn , Issue 15, 2007, Pages 2347-2350

Amberlyst-15 as a heterogeneous reusable catalyst for the synthesis of α-hydroxy phosphonates in water

(6) Tajbakhsh, Mahmood a Heydari, Akbar b Khalilzadeh, Mohammad A c Lakouraj, Moslem M a Zamenian, Behi a Khaksar, Samad b

a UNIVERSITY OF MAZANDARAN (Iran)

b TARBIAT MODARES UNIVERSITY (Iran)

c ISLAMIC AZAD UNIVERSITY (Iran)

Author keywords

hydroxy phosphonates; Abramov reaction; Amberlyst 15; Nucleophilic addition; Water

Indexed keywords

ALDEHYDE; ALPHA HYDROXY PHOSPHONATE; AMBERLYST 15; ANTINEOPLASTIC AGENT; ANTIVIRUS AGENT; ENZYME INHIBITOR; METHYLPHOSPHONIC ACID; PESTICIDE; PHOSPHONIC ACID DERIVATIVE; RENIN INHIBITOR; RESIN; UNCLASSIFIED DRUG; VACCINIA ANTIBODY; WATER;

ARTICLE; CATALYST; CHEMICAL REACTION; SYNTHESIS;

EID: 34948903704 PISSN: 09365214 EISSN: None Source Type: Journal
DOI: 10.1055/s-2007-985595 Document Type: Article

Times cited : (45)

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- Typical Procedure A solution of benzaldehyde (0.107 g, 1 mmol, trimethylphosphite (0.136 g, 1.1 mmol, and Amberlyst-15 (0.1 g) in H 2O (2 mL) was placed in a round-bottomed flask equipped with a magnetic stirrer and was heated at 50°C The stirring was continued for 1.5 h. After completion of the reaction as indicated by TLC, the reaction mixture was treated with aq sat. NaHCO3 solution followed by brine and the product was extracted three times with 5 mL CH2Cl2, dried over anhyd MgSO4, and concentrated to give an oily residue, which was crystallized to give 0.216 g (95, of dimethyl 1-hydroxy-1- phenylmethylphosphonate. Spectral Data for Selected Products Dimethyl 1-Hydroxy-1-phenylmethylphosphonate19 (Table 1, Entry 1) IR: 3260 (OH) cm-1. 1H NMR (500 MHz, CDCl3, δ, 3.6 (d, J, 10.3 Hz, 3 H, 3.6 (d, J, 10.3 Hz, 3 H, 5.0 d, 1 H, J, 13.2
- PC = 1.8 Hz, CH), 149.9 (s, CH).

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