Benzoic Acid → Benzyl Benzoate

Participants

Reaction Conditions

Reaction Steps

Methyl azodicarboxylate resin (6.55 g of 0.61 meq/g ~4.0 meq) was suspended in dry THF (100 ml) and allowed to swell for ~15 minutes. Benzoic acid (0.366 g, 3.0 mmol) was dissolved in THF (10 ml) and added to the resin. To the stirred mixture at 25° C. was added dropwise a solution of Ph3P (0.786 g, 3.0 mmol) and benzyl alcohol (0.361 ml, 3.5 mmol) in THF (5 ml). This mixture was left to stir at 25° C. for 16 hours. Resin was then filtered and washed with CH2Cl2 (4×150 mL) and Et2O. The filtrate and washings were concentrated in vacuo at 30° C. and flash chromatographed (3.5% EtOAC/hexane) to yield benzyl benzoate (0.417 g, 65%): IR (film) 1720 (vs), 1451 (m), 1272 (vs), 1110 (m), 710 (s), 697 (m) cm-1 ; 1H NMR (80 MHz, CDCl3) δ8.25-8.05 (m, 2H, o-PhCOO), 7.65-7.25 (m, 8H, m-, p-PhCOO, OCH2PH), 5.32 (s, 2H, OCH2Ph); EI-MS: 212.0839 (M+, 212.0837 calcd. for C14H12O2), 105.0343 (Base Peak, phC=O).

Provenance & Evidence