Reaction #1876826

Reaction equation

linalool

triethylamine

BOP Reagent

3-(2,4-dihydroxyphenyl)-acrylic acid

→

3-(2,4-dihydroxyphenyl)-acrylic acid 1,5-dimethyl-1-vinyl-hex-4-enyl ester

Solvents

THF

DMF

Conditions

Workup

1. 1
   OtherThe reaction mixture is partitioned between ether (200 mL) and water (400 mL)
2. 2
   Otherthe organic layer is removed
3. 3
   Washwashed with ether (200 mL)
4. 4
   WashThe combined organic layers are washed sequentially with saturated sodium bicarbonate solution (200 mL) and brine (200 mL)
5. 5
   DryingThe organic layer is dried over anhydrous magnesium sulfate, vacuum
6. 6
   Filtrationfiltered
7. 7
   Concentrationconcentrated

Procedure

To a solution of linalool (1.74 g, 11.3 mmol) and triethylamine (2.30 g, 22.6 mmol) in anhydrous THF (150 mL) stirred for 5 min at 22° C. is added 3-(2,4-dihydroxyphenyl)-acrylic acid (2.04 g, 11.3 mmol). To this heterogeneous solution is added BOP Reagent (5.00 g, 11.3 mmol; Aldrich #22,608-4) in DMF (10 mL), and the subsequent homogeneous reaction mixture is stirred for 1 h. The reaction mixture is partitioned between ether (200 mL) and water (400 mL); the organic layer is removed and washed with ether (200 mL). The combined organic layers are washed sequentially with saturated sodium bicarbonate solution (200 mL) and brine (200 mL). The organic layer is dried over anhydrous magnesium sulfate, vacuum filtered and concentrated to give 3-(2,4-dihydroxyphenyl)-acrylic acid 1,5-dimethyl-1-vinyl-hex-4-enyl ester as an oil that is purified by flash chromatography.

Source