Triethylamine → Phenylacetic Acid

HRID 1449240Notes

Reaction equation

HRID 1449240 reaction equation
N[C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=[O:10])=[CH:4][CH:3]=1.C(N(CC)CC)C>C(O)(C)(C)C>[C:5]1([CH2:8][C:9]([OH:11])=[O:10])[CH:6]=[CH:7][CH:2]=[CH:3][CH:4]=1

Participants

4

Reactant 2

HCID 8471TriethylamineHCID 145334-Aminophenylacetic acid

Product 1

HCID 999Phenylacetic AcidYield 113.5%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

A mixture of 8.3 g of 2-tosyltropone, 4.5 g of p-aminophenylacetic acid and 9 ml of triethylamine in 200 ml of tert-butylalcohol was refluxed for 24 hours. The mixture was concentrated and acidified with 2 N hydrochloric acid, followed by extraction with dichloromethane. The dichloromethane solution was extracted with a saturated sodium bicarbonate aqueous solution. The aqueous layer was acidified and extracted with dichloromethane. The dichloromethane solution was washed with water and dried over anhydrous magnesium sulfate and evaporated to give a yellow crystalline solid, which was recrystallized from ethanol to yield 4.6 g of p-(2-troponylamino) phenylacetic acid; m.p. 175°-176° C.; Analysis--Calculated for C15H13NO3 : C 70.58%, H 5.13%, N 5.49%; Found: C70.34%, H 5.30%, N 5.55%.

Workup

  1. temperaturewas refluxed for 24 hours
  2. concentrationThe mixture was concentrated
  3. extractionfollowed by extraction with dichloromethane
  4. extractionThe dichloromethane solution was extracted with a saturated sodium bicarbonate aqueous solution
  5. extractionextracted with dichloromethane
  6. washThe dichloromethane solution was washed with water
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customevaporated
  9. customto give a yellow crystalline solid, which
  10. customwas recrystallized from ethanol

Sources & evidence

ORD record
ord-f153508ec7974f9a977a094d300f17ad
Source dataset
uspto-grants-1980_02
Patent number
US04189607

Reaction notes

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