2-(4-Chloro-3-(hydroxymethyl)phenyl)ethanol → 2-Chloro-5-(2-hydroxyethyl)benzaldehyde

HRID 471129

Reaction equation

HRID 471129 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][OH:10])=[CH:4][C:3]=1[CH2:11][OH:12]>C(Cl)Cl.[O-2].[O-2].[Mn+4]>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][OH:10])=[CH:4][C:3]=1[CH:11]=[O:12]

Participants

4

Reactant 1

HCID 579892912-(4-Chloro-3-(hydroxymethyl)phenyl)ethanol

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 (example 61, step b) (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-a9012c1578a044dca9dd93736dc3a8ba
Source dataset
uspto-grants-2014_01
Patent number
US08629271B2

Linked notes

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