Dicyclohexylcarbodiimide → 4-Phenyloxane-2,6-dione

HRID 2256288Notes

Reaction equation

HRID 2256288 reaction equation
[C:1]1([CH:7]([CH2:12][C:13]([OH:15])=[O:14])[CH2:8][C:9]([OH:11])=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1(N=C=NC2CCCCC2)CCCCC1>C(Cl)Cl.CCCCCC>[C:1]1([CH:7]2[CH2:8][C:9](=[O:11])[O:15][C:13](=[O:14])[CH2:12]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 2

HCID 10868DicyclohexylcarbodiimideHCID 778233-Phenylglutaric acid

Product 1

HCID 2978824-Phenyloxane-2,6-dioneYield 58%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8058HexaneSolvent

Procedure

3-Phenylglutaric acid (100 g) in CH2Cl2 (800 mL) was treated with dicyclohexylcarbodiimide (104 g) in CH2Cl2 (400 mL) over 30 minutes. The resulting mixture was stirred at ambient temperature for 48 hours. The reaction mixture was then diluted with hexane (800 mL) and filtered. The filtrate was concentrated under reduced pressure and the residue crystallized from ethyl acetate/hexane to afford the title compound (53 g).

Workup

  1. filtrationfiltered
  2. concentrationThe filtrate was concentrated under reduced pressure
  3. customthe residue crystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-bfa02a5738d1447f8f3b60ca222b72af
Source dataset
uspto-grants-1997_08
Patent number
US05654316

Reaction notes

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