Triethylamine → HCID 54396231, compound

HRID 746062Notes

Reaction equation

HRID 746062 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]([O:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[C:11]([OH:17])[CH:10]=1)=[O:7].[CH2:18](OC1C=C(O)C=CC=1OC)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C(N(CC)CC)C.O1C=CC=C1C(Cl)=O>CN(C)C1C=CN=CC=1.C(Cl)Cl>[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]([O:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[C:11]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:10]=1)=[O:7]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 682422-Furancarbonyl chlorideHCID 135310983-(Benzyloxy)-4-methoxyphenolHCID 536654323-Hydroxy-4-methoxyphenyl 2-furancarboxylate

Product 1

HCID 54396231HCID 54396231, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

The compound 3-hydroxy-4-methoxyphenyl 2-furoate was made as follows. An amount of 2.00 gms. of 3-benzyloxy-4-methoxyphenol, 1.00 gms. of triethylamine and 0.10 gms of 4-dimethylaminopyridine were dissolved in 100 ml. of methylene chloride at 0° C. and stirred. To the mixture was added 1.16 gms. of 2-furoyl chloride and the mixture was stirred overnight. The mixture was then washed wth equal volumes of 1 M hydrochloric acid, saturated sodium bicarbonate and water. The mixture was then dried over magnesium sulfate and the solvent evaporated to yield 3-benzyloxy-4-methoxyphenyl 2-furoate.

Workup

  1. additionTo the mixture was added 1.16 gms
  2. washThe mixture was then washed wth equal volumes of 1 M hydrochloric acid, saturated sodium bicarbonate and water
  3. dry with materialThe mixture was then dried over magnesium sulfate
  4. customthe solvent evaporated

Sources & evidence

ORD record
ord-16eb3ae354704d8b9711e53fa1a92f52
Source dataset
uspto-grants-1986_07
Patent number
US04602095

Reaction notes

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