(3-Butoxy-5-hydroxymethyl-phenyl)-methanol → 5-Butoxyisophthalaldehyde

HRID 58977Notes

Reaction equation

HRID 58977 reaction equation
[CH2:1]([O:5][C:6]1[CH:7]=[C:8]([CH2:14][OH:15])[CH:9]=[C:10]([CH2:12][OH:13])[CH:11]=1)[CH2:2][CH2:3][CH3:4].C1C=C[NH+]=CC=1.[O-][Cr](Cl)(=O)=O>C(Cl)Cl>[CH2:1]([O:5][C:6]1[CH:11]=[C:10]([CH:12]=[O:13])[CH:9]=[C:8]([CH:7]=1)[CH:14]=[O:15])[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 57443335(3-Butoxy-5-hydroxymethyl-phenyl)-methanolHCID 178418287HCID 178418287, compound

Product 1

HCID 1177045015-ButoxyisophthalaldehydeYield 75.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(5-Butoxy-1,3-phenylene)dimethanol (0.24 g, 1.15 mmol) and CH2Cl2 (10 mL) were added to a round-bottom flask. To the solution was added PCC (0.74 g, 3.45 mmol), and the reaction was stirred at rt for 16 h. The reaction mixture was concentrated under reduced pressure. Purification by column chromatography (90% hexanes/EtOAc) afforded the desired product (0.18 g, 44%, 3 steps) as a white semi-solid. 1H NMR (300 MHz, CDCl3) δ ppm 9.99 (s, 2H), 7.89 (s, 1H), 7.58 (s, 21-1), 4.03 (t, J=6.6 Hz, 2H), 1.77 (quint, J=6.6 Hz, 2H), 1.47 (sext, J=7.2 Hz, 2H), 0.94 (t, J=7.5 Hz, 3H). 13C NMR (75 MHz, CDCl3) δ ppm 191.3, 160.6, 138.6, 124.2, 120.1, 68.9, 31.3, 19.4, 14.1.

Workup

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

Sources & evidence

ORD record
ord-8eb30809837346788db103a90896bc06
Source dataset
uspto-grants-2016_09
Patent number
US09439433B2

Reaction notes

Loading…