(3,4,5-Tris(benzyloxy)phenyl)methanol → 3,4,5-Tribenzyloxybenzaldehyde

HRID 2054546Notes

Reaction equation

HRID 2054546 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:14]=[C:15]([O:25][CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:16]=1[O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[CH2:12][OH:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1>C(Cl)Cl>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:14]=[C:15]([O:25][CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:16]=1[O:17][CH2:18][C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)[CH:12]=[O:13])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 11407668(3,4,5-Tris(benzyloxy)phenyl)methanolHCID 178418287HCID 178418287, compound

Product 1

HCID 18224183,4,5-TribenzyloxybenzaldehydeYield 91.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3,4,5-tribenzyloxy-benzyl alcohol 5 (8.9 g, 21 mmol) in methylene chloride (200 mL) at 0° C. was added pyridinium chlorochromate (5.43 g, 25 mmol) in small portions with vigorous stirring. The cooling was discontinued and reaction stirred at room temperature for 4 h. The dark brown suspension was filtered over a long pad of silica gel in a sintered glass funnel, and eluted with CH2Cl2, until all the pure product eluted out. The organic filtrate was evaporated down to give the pure product 6 as a soft white solid (8.1 g, 91.5% yield). 1H NMR (300 MHz, CDCl3): δ 5.16 (s, 6H, OCH2), 7.18 (s, 2H, 2,6-Ar—H), 7.26 -7.41 (m, 15H, Ar—H), 9.80 (s, 1H, CHO).

Workup

  1. customreaction
  2. filtrationThe dark brown suspension was filtered over a long pad of silica gel in a sintered glass funnel
  3. washeluted with CH2Cl2, until all the pure product
  4. washeluted out
  5. customThe organic filtrate was evaporated down

Sources & evidence

ORD record
ord-10d9cba0fa7b4d4b9936abd8af16e0a4
Source dataset
uspto-grants-2008_02
Patent number
US07329687B2

Reaction notes

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