4-Hydroxybenzaldehyde → 4-Formylphenyl 4'-methyl-[1,1'-biphenyl]-4-carboxylate

HRID 923566Notes

Reaction equation

HRID 923566 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([C:14]([OH:16])=[O:15])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.C(Cl)(=O)C(Cl)=O.O[C:24]1[CH:31]=[CH:30][C:27]([CH:28]=[O:29])=[CH:26][CH:25]=1>C(Cl)Cl.CN(C=O)C>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([C:14]([O:16][C:24]3[CH:31]=[CH:30][C:27]([CH:28]=[O:29])=[CH:26][CH:25]=3)=[O:15])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 1264-HydroxybenzaldehydeHCID 65578Oxalyl chlorideHCID 20634214'-Methyl-4-biphenylcarboxylic acid

Product 1

HCID 46687294-Formylphenyl 4'-methyl-[1,1'-biphenyl]-4-carboxylateYield 40.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent3×

Procedure

Prepared using General Procedure 2: To a stirred solution of 4′-methyl-[1,1′-biphenyl]-4-carboxylic acid (0.5 g, 2.35 mmol) in DCM (10 mL) was added DMF (3 drops) then oxalyl chloride (0.262 mL, 3.1 mmol) and left for 2 h. The reaction mixture was added to a solution of 4-hydroxybenzaldehyde (0.31 g, 2.6 mmol) and TEA (0.4 mL, 2.82 mmol) in DCM (10 mL) and stirred for 18 h. The reaction mixture was diluted with DCM (100 mL) and washed with NaHCO3 (100 mL). The organic layer was pre-absorbed onto silica gel and then purified by chromatography (EA/isohexanes) to afford 300 mg (40%) 4-formylphenyl 4′-methyl-[1,1′-biphenyl]-4-carboxylate INT-27 as a white solid. LCMS-ESI (m/z) calculated for C21H16O3: 316; no m/z observed, tR=4.25 min (Method 1).

Workup

  1. customPrepared
  2. washwashed with NaHCO3 (100 mL)
  3. customThe organic layer was pre-absorbed onto silica gel
  4. custompurified by chromatography (EA/isohexanes)

Sources & evidence

ORD record
ord-526553739ebf4d81ad8b007b9ac317ab
Source dataset
uspto-grants-2016_03
Patent number
US09278910B2

Reaction notes

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