2-ALLYL-3-HYDROXYBENZALDEHYDE

To a 3000 ml one neck, round bottom flask equipped with a condenser and thermometer was added allylether (7) (308 g) and tetrahydronaphthalene (300 mL). Compound (2) (600 g) was added to decahydronaphthalene (1800 ml) and the stirred reaction mixture was heated to 180 to 190 0C. Stirring was continued till completion of the reaction as monitored by HPLC. After completion, the reaction mixture was cooled and acetonitrile (4200 ml) was added to it. The acetonitrile layer was separated, concentrated. Toluene was added to the residue. The resulting mass was cooled, filtered. Optional treatment of the solid thus obtained using mixture of ethyl acetate and cyclohexane gave compound (3). Yield: 200 g (33.3percent)(0119) Potassium carbonate (100 g) was added to the solution of compound (3) (100 g) in DMF (200 ml). Allyl bromide (86.8 g) was gradually added to the reaction mixture and the resulting mixture was stirred at 25 to 35°C. (0120) After completion of the reaction, as monitored by TLC, the reaction mixture was quenched with water and extracted with methyl tertbutyl ether. The organic layer was concentrated to yield compound (4a). Yield: 110 g (88percent). (0121) JH NMR (300 MHz, DMSO-D6): delta 10.22 (s, 1H), 7.42 (m, 2H), 7.31 (dd, / = 5.85 and (0122) 1.14 Hz, 1H), 5.91 (m, 2H), 5.39 (m, 1H), 5.25 (m, 1H), 4.89 (m, 2H), 4.63 (m, 2H), 3.83 (0123) (m, 2H). (0124) M+H: 203.1Compound (3) (150 g) was added to the mixture of acetonitrile (750 ml) and potassium carbonate (192 g). The resultant mixture was stirred at 20 to 30 C followed by gradual addition of dimethyl sulfate (128 g) at the same temperature. The reaction mass was stirred at 20 to 45C, till completion, as monitored by HPLC. (0118) After completion, the reaction mixture was concentrated, and water (750 ml) was added to it. The resultant mass was stirred at 50 to 60 C, cooled and MTBE was added to it. The organic layer was separated and aqueous sodium hydroxide solution (14.8 g NaOH in 149 ml water was added to it with continuous stirring. Separation and concentration of the organic layer gave Compound (4beta). Yield: 148 g (90.8%).

Molecular Weight:162.18
XLogP3:2.1
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:3
Exact Mass:162.068079557
Monoisotopic Mass:162.068079557
Topological Polar Surface Area:37.3
Heavy Atom Count:12
Complexity:165
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes