Potassium Carbonate → 4-(3-Thienylmethoxy)-2-(2-trimethylsilylethoxy)methoxybenzoic acid

HRID 322952Notes

Reaction equation

HRID 322952 reaction equation
[S:1]1[CH:5]=[CH:4][C:3]([CH2:6][O:7][C:8]2[CH:17]=[CH:16][C:11]([C:12]([O:14]C)=[O:13])=[C:10]([O:18][CH2:19][O:20][CH2:21][CH2:22][Si:23]([CH3:26])([CH3:25])[CH3:24])[CH:9]=2)=[CH:2]1.C(=O)([O-])[O-].[K+].[K+]>CO>[S:1]1[CH:5]=[CH:4][C:3]([CH2:6][O:7][C:8]2[CH:17]=[CH:16][C:11]([C:12]([OH:14])=[O:13])=[C:10]([O:18][CH2:19][O:20][CH2:21][CH2:22][Si:23]([CH3:26])([CH3:25])[CH3:24])[CH:9]=2)=[CH:2]1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 22010432Methyl 4-(3-thienylmethoxy)-2-(2-trimethylsilylethoxy)methoxybenzoate

Product 1

HCID 220102164-(3-Thienylmethoxy)-2-(2-trimethylsilylethoxy)methoxybenzoic acidYield 51.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of methyl 4-(3-thienylmethoxy)-2-(2-trimethylsilylethoxy)methoxybenzoate (12.1 g) and aqueous potassium carbonate solution (50 mL; 10% w/v) in methanol (200 mL) is heated at reflux for 7 hours. It is then concentrated in vacuo and the residue is treated with water (200 mL) and acidified to pH 1 by treatment with hydrochloric acid (1 N), and the resulting solid is quickly filtered off and is then washed with water. The white solid is then azeotroped with cyclohexane in a Dean-Stark apparatus until no more water is removed. The solid is filtered off, to give 4-(3-thienylmethoxy)-2-(2-trimethylsilylethoxy)methoxybenzoic acid (6.03 g), in the form of a white solid.

Workup

  1. temperatureis heated
  2. temperatureat reflux for 7 hours
  3. concentrationIt is then concentrated in vacuo
  4. additionthe residue is treated with water (200 mL)
  5. filtrationthe resulting solid is quickly filtered off
  6. washis then washed with water
  7. customThe white solid is then azeotroped with cyclohexane in a Dean-Stark apparatus until no more water
  8. customis removed
  9. filtrationThe solid is filtered off

Sources & evidence

ORD record
ord-4456ea9b100f4da3970c600f7e145101
Source dataset
uspto-grants-2001_04
Patent number
US06211234B1

Reaction notes

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