Adipic Acid → Adipic acid monobenzyl ester

HRID 2196872Notes

Reaction equation

HRID 2196872 reaction equation
[CH:1]([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2].C(O)(=O)[CH2:12][CH2:13][CH2:14][CH2:15][C:16]([OH:18])=[O:17]>CCCCCCCC>[CH2:4]([O:3][C:1](=[O:2])[CH2:12][CH2:13][CH2:14][CH2:15][C:16]([OH:18])=[O:17])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

4

Reactant 2

HCID 196Adipic AcidHCID 7708Benzyl formate

Product 1

HCID 11075409Adipic acid monobenzyl esterYield 87%

Reagents, catalysts & solvents 1

HCID 356OctaneSolvent

Conditions

Temperature
100 °C

Procedure

DOWEX® 50W-X2 (2 g), benzyl formate (10 mL, mol), and adipic acid (2 g, mol) were added to octane (10 mL). The mixture was refluxed for 4 hours at 100° C., and the crude product was purified via silica chromatography to yield a clear, colorless liquid (87% yield). 1H NMR (CDCl3) 1.59-1.78 (m, 4H, CH2CH2), 2.33-2.39 (m, 4H, CH2COOH), 5.09 (s, 2H, PhCH2), 7.25-7.30 (m, 5H, aromatic).

Workup

  1. customthe crude product was purified via silica chromatography

Sources & evidence

ORD record
ord-c2f37d8ccb0a4b3dab7ace46dc3f17a9
Source dataset
uspto-grants-2012_12
Patent number
US08338492B2

Reaction notes

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