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

HRID 1458515Notes

Reaction equation

HRID 1458515 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 1E (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-5a27f481b60144058d2b11277db9b3f1
Source dataset
uspto-grants-1998_12
Patent number
US05851952

Reaction notes

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