Sodium Hydroxide → HCID 53781782, compound

Participants

Reaction Steps

To a stirred solution of 1.22 g (3.8 mmol) of trans-ethyl 2-(2,3,4-trimethoxyphenyl)cyclohexane-1-carboxylate in 20 mL of THF and 10 mL of methanol was added 10 mL of 10% aqueous NaOH. The mixture was stirred at room temperature for 18 h and heated at reflux for 18 h. After cooling, the bulk of the organic solvents was removed in vacuo and the residue was diluted with 100 mL of 5% aqueous NaOH and washed with 100 mL of ether. The aqueous layer was acidified to pH 1 with concentrated HCl and extracted with two 100 mL portions of ether. These ether extracts were combined, dried over MgSO4 and the solvent removed in vacuo to leave 0.88 g of trans-2-(2,3,4-trimethoxyphenyl)cyclohexane-1-carboxylic acid as an oil. 1H NMR (CDCl3) -- 1.3-2.2 (m, 8H), 2.65 (m, 1H), 3.1 (m, 1H), 3.8 (s, 9H), 6.6 (d, 1H), 6.8 (d, 1H).

Provenance & Evidence