Oxalyl chloride → 4-Formyl-3-methoxyphenyl 4-(heptyloxy)benzoate

HRID 923563Notes

Reaction equation

HRID 923563 reaction equation
[CH2:1]([O:8][C:9]1[CH:17]=[CH:16][C:12]([C:13]([OH:15])=[O:14])=[CH:11][CH:10]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7].C(Cl)(=O)C(Cl)=O.O[C:25]1[CH:32]=[CH:31][C:28]([CH:29]=[O:30])=[C:27]([O:33][CH3:34])[CH:26]=1>C(Cl)Cl.CN(C=O)C>[CH2:1]([O:8][C:9]1[CH:17]=[CH:16][C:12]([C:13]([O:15][C:25]2[CH:32]=[CH:31][C:28]([CH:29]=[O:30])=[C:27]([O:33][CH3:34])[CH:26]=2)=[O:14])=[CH:11][CH:10]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7]

Participants

6

Reactant 3

HCID 65578Oxalyl chlorideHCID 85154p-Heptoxybenzoic acidHCID 5195414-Hydroxy-2-Methoxybenzaldehyde

Product 1

HCID 892531414-Formyl-3-methoxyphenyl 4-(heptyloxy)benzoateYield 15.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent3×

Procedure

Prepared using General Procedure 2: To a stirred solution of 4-(heptyloxy)benzoic acid (1.41 g, 5.98 mmol) in DCM (10 mL) was added DMF (3 drops) and oxalyl chloride (0.589 mL, 6.87 mmol). After stirring for 2 h, the reaction mixture was added to a solution of 4-hydroxy-2-methoxybenzaldehyde (1 g, 6.57 mmol) and TEA (1.25 mL, 8.96 mmol) in DCM (10 mL) and stirred for 18 h. The reaction mixture was diluted with DCM (100 mL) and was washed with NaHCO3 (100 mL). The organic layer was pre-absorbed onto silica gel and purified by chromatography (EA/isohexanes) to afford 340 mg (15%) 4-formyl-3-methoxyphenyl 4-(heptyloxy)benzoate INT-25 as a white solid. LCMS-ESI (m/z) calculated for C22H26O5: 370; found 371 [M+H]+, tR=3.17 min (Method 10).

Workup

  1. customPrepared
  2. stirringstirred for 18 h
  3. washwas washed with NaHCO3 (100 mL)
  4. customThe organic layer was pre-absorbed onto silica gel
  5. custompurified by chromatography (EA/isohexanes)

Sources & evidence

ORD record
ord-f664b65ce2dd4d49a85d7482189d8527
Source dataset
uspto-grants-2016_03
Patent number
US09278910B2

Reaction notes

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