Tetrahydrofuran → Bis(p-dimethylaminophenyl)Methoxy Acetic Acid, Benzyl Ester

HRID 1995243Notes

Reaction equation

HRID 1995243 reaction equation
[CH3:1][N:2]([C:4]1[CH:20]=[CH:19][C:7]([CH:8]([OH:18])[C:9]2[CH:14]=[CH:13][C:12]([N:15]([CH3:17])[CH3:16])=[CH:11][CH:10]=2)=[CH:6][CH:5]=1)[CH3:3].COC.[C:24]([O:28][CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)(=[O:27])[CH2:25]O.O1CCCC1>CS(O)(=O)=O.CCCCCC>[CH3:17][N:15]([CH3:16])[C:12]1[CH:13]=[CH:14][C:9]([CH:8]([C:7]2[CH:19]=[CH:20][C:4]([N:2]([CH3:1])[CH3:3])=[CH:5][CH:6]=2)[O:18][CH2:25][C:24]([O:28][CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)=[O:27])=[CH:10][CH:11]=1

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 8254Dimethyl EtherHCID 927424,4'-Bis(dimethylamino)benzhydrolHCID 561337Benzyl 2-hydroxyacetate

Product 1

HCID 131712798Bis(p-dimethylaminophenyl)Methoxy Acetic Acid, Benzyl Ester

Reagents, catalysts & solvents 2

HCID 6395Methanesulfonic AcidCatalystHCID 8058HexaneSolvent

Procedure

A solution of 4,4'-bis(N,N-dimethylamino)benzhydrol, methyl ether (11.0 g, 0.039 mole), benzyl glycolate (6.6 g, 0.039 mole), 90 ml of tetrahydrofuran, 200 ml of hexane, and 10 drops of methanesulfonic acid was refluxed for 6 hours, replacing solvent as distillate was removed; then, 10 drops of tetramethylguanidine was added to discharge the color and the reaction mixture was filtered hot and cooled. A white solid formed which was filtered, washed with petroleum ether and then recrystallized from 4/1 hexane/acetone. The resulting white crystalline product had a mp 101.8°-103° C.

Workup

  1. customwas removed
  2. additionthen, 10 drops of tetramethylguanidine was added
  3. filtrationthe reaction mixture was filtered hot
  4. temperaturecooled
  5. customA white solid formed which
  6. filtrationwas filtered
  7. washwashed with petroleum ether
  8. customrecrystallized from 4/1 hexane/acetone

Sources & evidence

ORD record
ord-8c246ec41f024adeb8330005530377a3
Source dataset
uspto-grants-1983_09
Patent number
US04403792

Reaction notes

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