Ethyl 5-(hydroxymethyl)-4'-methylbiphenyl-3-carboxylate → Ethyl 5-formyl-4'-methylbiphenyl-3-carboxylate

HRID 1845257Notes

Reaction equation

HRID 1845257 reaction equation
[OH:1][CH2:2][C:3]1[CH:4]=[C:5]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH:6]=[C:7]([C:9]2[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][CH:10]=2)[CH:8]=1>C(Cl)Cl.[O-2].[Mn+4].[O-2]>[CH:2]([C:3]1[CH:4]=[C:5]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH:6]=[C:7]([C:9]2[CH:10]=[CH:11][C:12]([CH3:15])=[CH:13][CH:14]=2)[CH:8]=1)=[O:1]

Participants

4

Reactant 1

HCID 58188190Ethyl 5-(hydroxymethyl)-4'-methylbiphenyl-3-carboxylate

Product 1

HCID 58188063Ethyl 5-formyl-4'-methylbiphenyl-3-carboxylate

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of ethyl 5-(hydroxymethyl)-4′-methylbiphenyl-3-carboxylate (400 mg, 1.5 mmol) and manganese(IV) oxide (660 mg, 6.6 mmol) in methylene chloride (14 mL) was stirred at room temperature overnight. The reaction mixture was filtered through Celite and washed with methylene chloride. The filtrate was concentrated to afford the title compound.

Workup

  1. filtrationThe reaction mixture was filtered through Celite
  2. washwashed with methylene chloride
  3. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-e35decb50e3d4e4d9d5307a8910fa373
Source dataset
uspto-grants-2015_02
Patent number
US08946439B2

Reaction notes

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