Adipic Acid → HCID 22910791, compound

HRID 2399348Notes

Reaction equation

HRID 2399348 reaction equation
[CH3:1][O:2][C:3]1[CH:9]=[C:8]([OH:10])[CH:7]=[CH:6][C:4]=1[OH:5].[C:11](O)(=[O:19])[CH2:12][CH2:13][CH2:14][CH2:15][C:16]([OH:18])=[O:17].B(F)(F)F.CCOCC.O.O.O.C([O-])(=O)C.[Na+]>ClC(Cl)C.O>[OH:10][C:8]1[CH:9]=[C:3]([O:2][CH3:1])[C:4]([OH:5])=[CH:6][C:7]=1[C:11](=[O:19])[CH2:12][CH2:13][CH2:14][CH2:15][C:16]([OH:18])=[O:17]

Participants

7

Reactant 4

HCID 196Adipic AcidHCID 8000Boron trifluoride etherateHCID 699882-Methoxybenzene-1,4-diolHCID 23665404Sodium Acetate Trihydrate

Product 1

HCID 22910791HCID 22910791, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 63651,1-DichloroethaneSolvent

Procedure

Seven grams of 2-methoxyhydroquinone and 13.6 g of the monomethyl ester of adipic acid in 60 ml of dichloroethane are mixed under nitrogen in a three-necked flask. Thirteen milliliters of boron trifluoride etherate is run in at room temperature. After five hours of refluxing, the reaction medium is poured into a mixture of 40 g of sodium acetate trihydrate and 100 ml of water. The product is extracted with 500 ml of ethyl acetate, washed, dried, and concentrated under vacuum. The residue is treated with a mixture of 1.4 ml of concentrated sulfuric acid, 14 ml of water, and 40 ml of acetic acid at 80° C. for three hours, then the solution is poured into 100 ml of ice water. The precipitate is filtered, washed several times with 20 ml of water, and dried. The solid is recrystallized from a mixture of ethyl acetate and isopropyl ether, yielding yellow crystals with the following characteristics:

Workup

  1. customis run in at room temperature
  2. temperatureAfter five hours of refluxing
  3. extractionThe product is extracted with 500 ml of ethyl acetate
  4. washwashed
  5. customdried
  6. concentrationconcentrated under vacuum
  7. additionThe residue is treated with a mixture of 1.4 ml of concentrated sulfuric acid, 14 ml of water, and 40 ml of acetic acid at 80° C. for three hours
  8. additionthe solution is poured into 100 ml of ice water
  9. filtrationThe precipitate is filtered
  10. washwashed several times with 20 ml of water
  11. customdried
  12. customThe solid is recrystallized from a mixture of ethyl acetate and isopropyl ether
  13. customyielding yellow crystals with the following characteristics

Sources & evidence

ORD record
ord-1c786e010d504942a616a19306e39c3d
Source dataset
uspto-grants-1995_09
Patent number
US05449518

Reaction notes

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