Boron trifluoride etherate → HCID 20437362, compound

HRID 615043Notes

Reaction equation

HRID 615043 reaction equation
[CH2:1]([NH:17][C:18]1[CH:26]=[CH:25][C:21]([C:22]([OH:24])=[O:23])=[CH:20][CH:19]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16].B(F)(F)F.[CH3:31]COCC>CO>[CH2:1]([NH:17][C:18]1[CH:19]=[CH:20][C:21]([C:22]([O:24][CH3:31])=[O:23])=[CH:25][CH:26]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16]

Participants

4

Reactant 2

HCID 8000Boron trifluoride etherateHCID 472634-(Hexadecylamino)benzoic acid

Product 1

HCID 20437362HCID 20437362, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 50.5 g of 4-(n-hexadecylamino)benzoic acid and 34.4 ml of boron trifluoride etherate in 200 ml of methanol is stirred under reflux for 44 hours, allowed to cool, and is poured into 1.20 liters of ice cold 5% aqueous sodium carbonate solution. The white solid is collected by filtration and recrystallized from benzene-ethanol to yield methyl 4-(n-hexadecylamino)benzoate, mp 92°-93° C.

Workup

  1. temperatureunder reflux for 44 hours
  2. temperatureto cool
  3. filtrationThe white solid is collected by filtration
  4. customrecrystallized from benzene-ethanol

Sources & evidence

ORD record
ord-4a2a700978f24b288783be2f5caf0665
Source dataset
uspto-grants-1979_03
Patent number
US04146546

Reaction notes

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