Methyl 2-chloro-4-(hydroxymethyl)benzoate → Methyl 2-chloro-4-formylbenzoate

HRID 2178090Notes

Reaction equation

HRID 2178090 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]([CH2:12][OH:13])[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5]>ClCCl.[O-2].[Mn+2]>[Cl:1][C:2]1[CH:11]=[C:10]([CH:12]=[O:13])[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5]

Participants

4

Reactant 1

HCID 19780655Methyl 2-chloro-4-(hydroxymethyl)benzoate

Product 1

HCID 57461225Methyl 2-chloro-4-formylbenzoateYield 62.2%

Reagents, catalysts & solvents 2

HCID 160959Manganese oxideCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
27 °C

Procedure

A mixture of methyl 2-chloro-4-(hydroxymethyl)benzoate (350 mg, 1.7 mmol) in and manganese oxide (756 mg, 30.9 mmol) in dichloromethane (10 mL) was stirred at 27° C. for 6 hours. The mixture was filtered and evaporated in vacuo to give Intermediate 75 (210 mg, 61%).

Workup

  1. filtrationThe mixture was filtered
  2. customevaporated in vacuo

Sources & evidence

ORD record
ord-c50c1a8049f24f3f9d5a9c6552ef9277
Source dataset
uspto-grants-2015_06
Patent number
US09067893B2

Reaction notes

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