Dicyclohexylcarbodiimide → HCID 53800654, compound

HRID 1463015Notes

Reaction equation

HRID 1463015 reaction equation
[CH2:1]([C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1)[CH2:2][CH3:3].[CH2:11]([CH:16]1[O:21][C:20]2[CH:22]=[CH:23][C:24]([C:26](O)=[O:27])=[CH:25][C:19]=2[CH2:18][O:17]1)[CH2:12][CH2:13][CH2:14][CH3:15].C1(N=C=NC2CCCCC2)CCCCC1>CN(C)C1C=CN=CC=1.C(Cl)Cl>[CH2:1]([C:4]1[CH:9]=[CH:8][C:7]([O:10][C:26]([C:24]2[CH:23]=[CH:22][C:20]3[O:21][CH:16]([CH2:11][CH2:12][CH2:13][CH2:14][CH3:15])[O:17][CH2:18][C:19]=3[CH:25]=2)=[O:27])=[CH:6][CH:5]=1)[CH2:2][CH3:3]

Participants

6

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 125804-PropylphenolHCID 20450693HCID 20450693, compound

Product 1

HCID 53800654HCID 53800654, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

0.1 g of 4-(dimethylamino)pyridine and 1.6 g of p-propylphenol are added to a solution of 2.5 g of 2-pentyl-1,3-benzodioxan-6-carboxylic acid in 50 ml of methylene chloride. The mixture is treated portionwise at 0° C. while stirring with 2.4 g of N,N'-dicyclohexylcarbodiimide. After completion of the addition, the mixture is stirred at 0° C. for a further 10 minutes and then at room temperature for 3 hours. The precipitate is filtered off and the filtrate is evaporated. The residue is taken up in 40 ml of methylene chloride and again filtered. The filtrate is washed with saturated sodium carbonate solution and then with water, dried over sodium sulphate, filtered and evaporated. The crude product is dissolved in boiling hexane, filtered hot with active carbon and crystallized from the filtrate. The crystallizate is recrystallized twice more from hexane. There is obtained pure 2-pentyl-1,3-benzodioxan-6-carboxylic acid p-propylphenyl ester; m.p. 97.5° C., cl.p. 74.5° C. (monotropic).

Workup

  1. additionThe mixture is treated portionwise at 0° C.
  2. additionAfter completion of the addition
  3. waitat room temperature for 3 hours
  4. filtrationThe precipitate is filtered off
  5. customthe filtrate is evaporated
  6. filtrationagain filtered
  7. washThe filtrate is washed with saturated sodium carbonate solution
  8. dry with materialwith water, dried over sodium sulphate
  9. filtrationfiltered
  10. customevaporated
  11. dissolutionThe crude product is dissolved
  12. filtrationfiltered hot with active carbon
  13. customcrystallized from the filtrate
  14. customThe crystallizate is recrystallized twice more from hexane

Sources & evidence

ORD record
ord-10571e913f3b4d7e8d46c603504e657d
Source dataset
uspto-grants-1984_07
Patent number
US04462923

Reaction notes

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