Dicyclohexylcarbodiimide → Phenoxyacetoxysuccinimide

HRID 435433Notes

Reaction equation

HRID 435433 reaction equation
[O:1]([CH2:8][C:9]([OH:11])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O[N:13]1[C:17](=[O:18])[CH2:16][CH2:15][C:14]1=[O:19].C1(N=C=NC2CCCCC2)CCCCC1>C(OCC)(=O)C>[O:1]([CH2:8][C:9]([O:11][N:13]1[C:17](=[O:18])[CH2:16][CH2:15][C:14]1=[O:19])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 19188Phenoxyacetic AcidHCID 80170N-Hydroxysuccinimide

Product 1

HCID 190981PhenoxyacetoxysuccinimideYield 60.2%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A suspension of phenoxyacetic acid (15.2 g, 100 mmol) and N-hydroxysuccinimide (11.5 g, 100 mmol) in ethyl acetate (300 ml) was cooled in an ice bath, treated with N,N'-dicyclohexylcarbodiimide (20.6 g, 100 mmol) and stirred for 1 hour at 0° and then overnight at room temperature. The precipitate which formed was filtered; the filtrate was evaporated to dryness; and the residue was crystallized from ethyl acetate to yield 15.0 g of N-(phenoxyacetyloxy)succinimide.

Workup

  1. temperaturewas cooled in an ice bath
  2. customovernight
  3. customat room temperature
  4. customThe precipitate which formed
  5. filtrationwas filtered
  6. customthe filtrate was evaporated to dryness
  7. customand the residue was crystallized from ethyl acetate

Sources & evidence

ORD record
ord-dfc507f4d4de450b92004a211b863d11
Source dataset
uspto-grants-1983_08
Patent number
US04401660

Reaction notes

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