Benzoic Acid → Benzyl Benzoate

HRID 1087869Notes

Reaction equation

N(C(OC)=O)=NC([O-])=O.[C:10]([OH:18])(=[O:17])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[CH2:38](O)[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1>C1COCC1>[C:10]([O:18][CH2:38][C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)(=[O:17])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

Conditions

Temperature: 25 °C

Procedure

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).

Workup

waitto swell for ~15 minutes
additionadded to the resin
waitThis mixture was left
filtrationResin was then filtered
washwashed with CH2Cl2 (4×150 mL) and Et2O
concentrationThe filtrate and washings were concentrated in vacuo at 30° C.
customflash chromatographed (3.5% EtOAC/hexane)

Sources & evidence

ORD record: ord-2da2f63aa6844b60b623961214dfbc69
Source dataset: uspto-grants-1990_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04960832

Reaction notes

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