(5-(2-Ethylbutoxy)-1,3-phenylene)dimethanol → 5-(2-Ethylbutoxyl)isophthalaldehyde

HRID 58993Notes

Reaction equation

HRID 58993 reaction equation
[CH2:1]([CH:3]([CH2:16][CH3:17])[CH2:4][O:5][C:6]1[CH:7]=[C:8]([CH2:14][OH:15])[CH:9]=[C:10]([CH2:12][OH:13])[CH:11]=1)[CH3:2].C1C=C[NH+]=CC=1.[O-][Cr](Cl)(=O)=O>C(Cl)Cl>[CH2:16]([CH:3]([CH2:1][CH3:2])[CH2:4][O:5][C:6]1[CH:11]=[C:10]([CH:12]=[O:13])[CH:9]=[C:8]([CH:7]=1)[CH:14]=[O:15])[CH3:17]

Participants

4

Reactant 2

HCID 117704465(5-(2-Ethylbutoxy)-1,3-phenylene)dimethanolHCID 178418287HCID 178418287, compound

Product 1

HCID 1177045835-(2-Ethylbutoxyl)isophthalaldehydeYield 26.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(5-(2-Ethylbutoxy)-1,3-phenylene)dimethanol (0.50 g, 2.10 mmol) and CH2Cl2 (10 mL) were added to a round-bottom flask. To this solution was added PCC (1.35 g, 6.30 mmol), and the reaction was stirred for 16 h. The reaction mixture was concentrated under reduced pressure. Purification by column chromatography (90% hexanes/EtOAc) afforded the desired product (0.13 g, 25%, 3 steps) as a white semi-solid. 1H NMR (500 MHz, CDCl3) δ ppm 10.01 (s, 2H), 7.90 (s, 1H), 7.62 (s, 2H), 3.94 (d, J=5.5 Hz, 2H), 1.68 (hept, J=6.5 Hz, 1H), 1.46 (dec, J=6.5 Hz, 4H), 0.91 (t, J=7.5 Hz, 6H). 13C NMR (125 MHz, CDCl3) δ ppm 191.1, 160.7, 138.5, 124.1, 120.0, 71.1, 40.9, 23.5, 11.3.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customPurification by column chromatography (90% hexanes/EtOAc)

Sources & evidence

ORD record
ord-2cfb12f92eec49f4866396f9e007da00
Source dataset
uspto-grants-2016_09
Patent number
US09439433B2

Reaction notes

Loading…