Water → 2-[4-(4-Hydroxybutyl)phenoxymethyl]-3-thiophenecarboxylic acid

HRID 638258Notes

Reaction equation

HRID 638258 reaction equation
C[O:2][C:3]([C:5]1[CH:9]=[CH:8][S:7][C:6]=1[CH2:10][O:11][C:12]1[CH:17]=[CH:16][C:15]([CH2:18][CH2:19][CH2:20][CH2:21][OH:22])=[CH:14][CH:13]=1)=[O:4].[OH-].[K+].O>C(O)C>[OH:22][CH2:21][CH2:20][CH2:19][CH2:18][C:15]1[CH:14]=[CH:13][C:12]([O:11][CH2:10][C:6]2[S:7][CH:8]=[CH:9][C:5]=2[C:3]([OH:4])=[O:2])=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 962WaterHCID 14797Potassium HydroxideHCID 136039402-[4-(4-Hydroxybutyl)phenoxymethyl]-3-thiophenecarboxylic acid methyl ester

Product 1

HCID 136039412-[4-(4-Hydroxybutyl)phenoxymethyl]-3-thiophenecarboxylic acidYield 88%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A stirred solution of 7.96 g of 2-[4-(4-hydroxybutyl)phenoxymethyl]-3-thiophenecarboxylic acid methyl ester, 14.41 g of potassium hydroxide, 15 ml of water and 100 ml of 95% ethanol was refluxed for one hour. The solution was concentrated. The residue was diluted with 200 ml of water and the solution was extracted once with ether. The aqueous phase was acidified with concentrated hydrochloric acid, with cooling, and the precipitate was collected, washed with water and dried in vacuo at 40° C. overnight over sodium hydroxide pellets. Recrystallization from 20 ml of 95% ethanol gave 6.62 g (88%) of product, m.p. 139.5°-141° C.

Workup

  1. concentrationThe solution was concentrated
  2. additionThe residue was diluted with 200 ml of water
  3. extractionthe solution was extracted once with ether
  4. temperaturewith cooling
  5. customthe precipitate was collected
  6. washwashed with water
  7. dry with materialdried in vacuo at 40° C. overnight over sodium hydroxide pellets
  8. customRecrystallization from 20 ml of 95% ethanol

Sources & evidence

ORD record
ord-62abd137727d4cc5a30a948a74f35fcb
Source dataset
uspto-grants-1985_12
Patent number
US04560701

Reaction notes

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