Dimethylformamide → HCID 11601560, compound

HRID 2390593Notes

Reaction equation

HRID 2390593 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]([OH:20])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15]CCCO.CN(C)C=O.[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=O.[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1.[C:47]([O:50]CC)(=[O:49])[CH3:48]>>[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8](=[O:20])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:48][C:47]([OH:50])=[O:49]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 8857Ethyl AcetateHCID 2724130Cornforth reagentHCID 57435539HCID 57435539, compound

Product 1

HCID 11601560HCID 11601560, compoundYield 10%

Procedure

A 100 mL flask was charged with 1-(2-Hydroxy-phenyl)-undecane-1,11-diol (5.0 g, 18.9 mmol) and 50 mL of dimethyl formamide. To this was added pyridinium dichromate (32.9 g, 87.5 mmol). (The addition was mildly exothermic.) The reaction mixture was stirred at room temperature overnight. The reaction mixture was poured into 50 mL of ethyl acetate and washed with 200 mL of water, 30 mL of 4% aqueous hydrochloric acid, 30 mL water, and finally with 30 mL of brine. The organic layer was then stirred with 10 g of silica gel for 15 minutes, dried with sodium sulfate, filtered, and solvent removed under reduced pressure. The off-white crude product was recrystallized from ethanol/water. The product (0.5 g, 10%) was isolated as an off-white solid, mp 85-87° C. Combustion analysis: Found: C, 69.01, H, 8.36%; C16H22O4 requires C, 69.54; H, 8.02%; 1H NMR (d6-DMSO): δ 12.0, s, 1H (COOH); δ 7.9 dd, 1H (aryl H); δ 7.5, dt, 1H, (aryl H); δ 6.9, complex multiplet, 2H (aryl H's), 3.1, t, 2H (CH2 α to carbonyl); δ 2.2, t, 2H(CH2 α to COOH); δ 1.6, multiplet, 2H (CH2 β to carbonyl), δ 1.5, multiplet, 2H (CH2 β to COOH), δ 1.3, multiplet, 8H (rest of CH2's).

Workup

  1. addition(The addition
  2. washwashed with 200 mL of water, 30 mL of 4% aqueous hydrochloric acid, 30 mL water
  3. stirringThe organic layer was then stirred with 10 g of silica gel for 15 minutes
  4. dry with materialdried with sodium sulfate
  5. filtrationfiltered
  6. customsolvent removed under reduced pressure
  7. customThe off-white crude product was recrystallized from ethanol/water

Sources & evidence

ORD record
ord-4df6a09bf1b44e2e8a188c09729b318e
Source dataset
uspto-grants-2012_09
Patent number
US08273794B2

Reaction notes

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