4-Methoxyphenylacetic Acid → HCID 67184281, compound

HRID 1958683Notes

Reaction equation

HRID 1958683 reaction equation
COC1C=CC(CC(O)=O)=CC=1.[Cl:13][C:14]1[CH:23]=[CH:22][CH:21]=[CH:20][C:15]=1[C:16](OC)=O.[CH3:24][O:25][C:26]1[CH:31]=[CH:30][C:29]([C:32]2[CH:33]=[C:34]([C:37]([O-:39])=[O:38])[S:35]C=2)=[CH:28][CH:27]=1.[OH-].[Na+]>O1CCOCC1.CO>[Cl:13][C:14]1[CH:23]=[CH:22][CH:21]=[CH:20][C:15]=1[C:16]1[S:35][C:34]([C:37]([OH:39])=[O:38])=[CH:33][C:32]=1[C:29]1[CH:28]=[CH:27][C:26]([O:25][CH3:24])=[CH:31][CH:30]=1

Participants

7

Reactant 4

HCID 76904-Methoxyphenylacetic AcidHCID 11895Methyl 2-chlorobenzoateHCID 14798Sodium HydroxideHCID 6930993HCID 6930993, compound

Product 1

HCID 67184281HCID 67184281, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
55 °C

Procedure

5-(2-Chlorophenyl)-4-(4-methoxyphenyl)thiophene-2-carboxylic acid is prepared, according to the procedure used in stages 1A)-1E), from (4-methoxyphenyl)acetic acid and methyl 2-chlorobenzoate. In the final stage of this procedure, 5 g of methyl 542-chlorophenyl)-4-(4-methoxyphenyl)-2-thiophenecarboxylate and 1.11 g of sodium hydroxide pellets are added to 30 ml of methanol and 3 ml of dioxane. The reaction medium is heated at 50-60° C. for 5 hours. It is evaporated to dryness, water is added and the impurities are extracted with ether. The aqueous phase is acidified and the expected compound is extracted with ether. After drying and evaporating, 3.5 g of the expected compound are obtained.

Workup

  1. custom5-(2-Chlorophenyl)-4-(4-methoxyphenyl)thiophene-2-carboxylic acid is prepared
  2. customIt is evaporated to dryness, water
  3. additionis added
  4. extractionthe impurities are extracted with ether
  5. extractionthe expected compound is extracted with ether
  6. customAfter drying
  7. customevaporating

Sources & evidence

ORD record
ord-0181be645ad54182b57b81c5e8d0686a
Source dataset
uspto-grants-2013_04
Patent number
US08410137B2

Reaction notes

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