Diethyl Ether → Oxalic acid, di(2-phenylethyl) ester

HRID 630569Notes

Reaction equation

HRID 630569 reaction equation
[C:1](Cl)(=[O:5])[C:2](Cl)=[O:3].[C:7]1([CH2:13][CH2:14][OH:15])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.CC[O:18][CH2:19][CH3:20]>N1C=CC=CC=1>[C:7]1([CH2:13][CH2:14][O:15][C:1](=[O:5])[C:2]([O:18][CH2:19][CH2:20][C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[O:3])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 60542-PhenylethanolHCID 65578Oxalyl chloride

Product 1

HCID 6421929Oxalic acid, di(2-phenylethyl) esterYield 84%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Oxalyl chloride (10.2 g, 80.4 mmol) was added dropwise during 20 min to a stirred solution of 2-phenylethanol (20.0 g, 163.7 mmol) in pyridine (165 mL) at 0° C. The reaction mixture was allowed to warm to room temperature overnight. Ether was added (300 mL, 2×) and the mixture extracted with H2SO4 (10%, 300 mL, 3×), a saturated solution of NaHCO3 (300 mL, 3×) and a saturated solution of NaCl (300 mL, 2×, pH 6). The organic layer was dried (Na2SO4) and concentrated. Column chromatography (SiO2, heptane/diethyl ether 1:1) gave 20.1 g (84%) of a solid.

Workup

  1. extractionthe mixture extracted with H2SO4 (10%, 300 mL, 3×)
  2. dry with materialThe organic layer was dried (Na2SO4)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-363516799f42470bb2b751fd2b0f21f7
Source dataset
uspto-grants-2016_04
Patent number
US09315763B2

Reaction notes

Loading…