5-(Carboxymethyl)-2-chlorobenzoic acid → 2-Chloro-5-(2-hydroxyethyl)benzaldehyde

HRID 1255242Notes

Reaction equation

HRID 1255242 reaction equation
[C:1]([CH2:4][C:5]1[CH:6]=[CH:7][C:8]([Cl:14])=[C:9]([CH:13]=1)[C:10](O)=[O:11])(O)=[O:2]>C(Cl)Cl.[O-2].[O-2].[Mn+4]>[Cl:14][C:8]1[CH:7]=[CH:6][C:5]([CH2:4][CH2:1][OH:2])=[CH:13][C:9]=1[CH:10]=[O:11]

Participants

4

Reactant 1

HCID 579893705-(Carboxymethyl)-2-chlorobenzoic acid2×

Product 1

HCID 579893312-Chloro-5-(2-hydroxyethyl)benzaldehyde

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

Manganese (IV) dioxide (1.00 g) was added to a solution of 2-(4-chloro-3-(hydroxymethyl)phenyl)ethanol [Aromatic Intermediate 7, step c] (0.200 g) in DCM (5 mL), and the resulting suspension was stirred at room temperature overnight. The mixture was then filtered through Celite, washing the residue well with DCM. The filtrate and washings were concentrated in vacuo to afford the subtitled compound as a colourless oil. Yield 0.197 g.

Workup

  1. filtrationThe mixture was then filtered through Celite
  2. washwashing the residue well with DCM
  3. concentrationThe filtrate and washings were concentrated in vacuo

Sources & evidence

ORD record
ord-e5b402bbde5f48b0ae84dbe57e5b46c6
Source dataset
uspto-grants-2013_06
Patent number
US08455483B2

Reaction notes

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