Water → HCID 18916177, compound

HRID 1290600Notes

Reaction equation

HRID 1290600 reaction equation
[NH2:1][C:2]1[CH:13]=[CH:12][C:5]([C:6]([O:8][CH2:9][CH:10]=[CH2:11])=[O:7])=[CH:4][CH:3]=1.C(N(CC)CC)C.[C:21]([C:25]1[CH:26]=[C:27]([CH:31]=[CH:32][C:33]=1[O:34][CH3:35])[C:28](Cl)=[O:29])([CH3:24])([CH3:23])[CH3:22].O>C1COCC1>[C:21]([C:25]1[CH:26]=[C:27]([CH:31]=[CH:32][C:33]=1[O:34][CH3:35])[C:28]([NH:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([O:8][CH2:9][CH:10]=[CH2:11])=[O:7])=[CH:12][CH:13]=1)=[O:29])([CH3:24])([CH3:22])[CH3:23]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 13075143Prop-2-en-1-yl 4-aminobenzoateHCID 136335553-Tert-butyl-4-methoxybenzoyl chloride

Product 1

HCID 18916177HCID 18916177, compoundYield 42.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

In a round bottom flask, there are introduced 5.92 g (33.4 mmoles) of allyl 4-aminobenzoate, 5.6 ml (40.25 mmoles) of triethylamine and 100 ml of THF. A solution of 8 g (38.4 mmoles) of 3-tert.butyl-4-methoxybenzoyl chloride dissolved in 50 ml of THF are slowly added and the mixture is stirred at ambient temperature for 4 hours. The reaction medium is poured into water and extracted with dichloromethane. The organic phase is decanted, washed with demineralized water up to pH 6, dried on Na2SO4 and filtered. The solvents are evaporated under reduced pressure. The resulting maroon oil is crystallized in hexane. The solid is filtered and recrystallized in absolute ethanol. After filtration on fritted glass and drying for 48 hours at 80° C. 5.1 g (42.5%) of the expected ester are obtained in the form of white crystals whose melting point is 180°-182° C.

Workup

  1. additionare slowly added
  2. extractionextracted with dichloromethane
  3. customThe organic phase is decanted
  4. washwashed with demineralized water up to pH 6
  5. customdried on Na2SO4
  6. filtrationfiltered
  7. customThe solvents are evaporated under reduced pressure
  8. customThe resulting maroon oil is crystallized in hexane
  9. filtrationThe solid is filtered
  10. customrecrystallized in absolute ethanol
  11. filtrationAfter filtration on fritted glass
  12. customdrying for 48 hours at 80° C

Sources & evidence

ORD record
ord-290cd28f3e874586ab0323080afb7d31
Source dataset
uspto-grants-1998_05
Patent number
US05753239

Reaction notes

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