Dimethylformamide → HCID 20230522, compound

HRID 2290805Notes

Reaction equation

HRID 2290805 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]([OH:16])=O)[CH:5]=[CH:6][C:7]=1[OH:8].[CH2:17](Cl)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C(=O)([O-])[O-].[K+].[K+].CN(C)[CH:33]=[O:34]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.[I-].[K+].O>[CH2:17]([O:1][C:2]1[CH:3]=[C:4]([CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]([O:34][CH2:33][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[O:16])[CH:5]=[CH:6][C:7]=1[O:8][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

8

Reactant 4

HCID 6228DimethylformamideHCID 7503Benzyl ChlorideHCID 11430Potassium CarbonateHCID 13519335HCID 13519335, compound

Product 1

HCID 20230522HCID 20230522, compound

Reagents, catalysts & solvents 3

HCID 4875Potassium IodideCatalystHCID 74236Tetrabutylammonium BromideCatalystHCID 962WaterSolvent

Procedure

A mixture of 3.8 g of 6-(3,4-dihydroxyphenyl)hexanoic acid, 8.6 g of benzyl chloride, 9.4 g of potassium carbonate, 0.1 g of potassium iodide, 0.1 g of tetra-n-butylammonium bromide, and 50 ml of N,N-dimethylformamide was stirred overnight at room temperature. After the reaction was over, 200 ml of water was added to the reaction mixture and the product was extracted three times each time with 100 ml of ether. The extracts were combined with each other, washed with water, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to provide a sticky product. The product was applied to silica gel (150 ml) column chromatography and eluted with a mixture of toluene and ethyl acetate (19:1) to provide 3.4 g of benzyl 6-(3,4-dibenzyloxyphenyl)hexanate.

Workup

  1. additionwas added to the reaction mixture
  2. extractionthe product was extracted three times each time with 100 ml of ether
  3. washwashed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customto provide a sticky product
  7. washeluted with a mixture of toluene and ethyl acetate (19:1)

Sources & evidence

ORD record
ord-f7e21f188c3e461cabb5423a5c7660c7
Source dataset
uspto-grants-1986_10
Patent number
US04618627

Reaction notes

Loading…