Sulfuric Acid → (3-Benzyloxy-5-trifluoromethylthien-2-yl)-carboxylic acid

HRID 2229116Notes

Reaction equation

HRID 2229116 reaction equation
[CH2:1]([O:8][C:9]1[CH:13]=[C:12]([C:14]([F:17])([F:16])[F:15])[S:11][C:10]=1[C:18]([O:20]C)=[O:19])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O1CCCC1.S(=O)(=O)(O)O>[OH-].[Na+]>[CH2:1]([O:8][C:9]1[CH:13]=[C:12]([C:14]([F:15])([F:16])[F:17])[S:11][C:10]=1[C:18]([OH:20])=[O:19])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 8028TetrahydrofuranHCID 11278508Methyl (3-benzyloxy-5-trifluoromethylthien-2-yl)-carboxylate

Product 1

HCID 11426602(3-Benzyloxy-5-trifluoromethylthien-2-yl)-carboxylic acidYield 89%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

A mixture of 5E (3.80 g) and tetrahydrofuran (12 ml) was heated to reflux in 2N sodium hydroxide (12 ml) for 12 hours. Then the mixture was poured on ice and acidified with 6N sulfuric acid (pH=1-2). The mixture is extracted with diethyl ether twice. The combined organic phases were washed with water and dried. The mixture was concentrated and the residue is distilled under reduced pressure to yield the product as a white solid (3.22 g, 89%) with a melting point of 142-144° C.

Workup

  1. temperaturewas heated
  2. additionThen the mixture was poured on ice
  3. extractionThe mixture is extracted with diethyl ether twice
  4. washThe combined organic phases were washed with water
  5. customdried
  6. concentrationThe mixture was concentrated
  7. distillationthe residue is distilled under reduced pressure

Sources & evidence

ORD record
ord-955a3a62499a4c0bb093db16e8b1709e
Source dataset
uspto-grants-2002_07
Patent number
US06420315B1

Reaction notes

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