Methanol → HCID 21268558, compound

HRID 1194817Notes

Reaction equation

HRID 1194817 reaction equation
[CH3:1][C:2]1[CH:24]=[CH:23][C:5]([C:6]([C:8]2[C:16]3[O:15][CH2:14][CH2:13][C:12]=3[CH:11]=[C:10]([CH2:17][C:18]([O:20]CC)=[O:19])[CH:9]=2)=[S:7])=[CH:4][CH:3]=1.CO.[OH-].[Na+]>O>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([C:8]2[C:16]3[O:15][CH2:14][CH2:13][C:12]=3[CH:11]=[C:10]([CH2:17][C:18]([OH:20])=[O:19])[CH:9]=2)=[S:7])=[CH:23][CH:24]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 21268560HCID 21268560, compound

Product 1

HCID 21268558HCID 21268558, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of ethyl 7-(4-methylthiobenzoyl)-2,3-dihydrobenzofuran-5-ylacetate (10.0 g), 50 ml of methanol, 200 ml of water, and 4 g of sodium hydroxide was heated at reflux for approximately 2 hours. The reaction mixture was cooled and washed with ether. The ether washed aqueous residue was acidified with dilute hydrochloric acid and then extracted with ethyl acetate. The combined organic extracts were washed with water and evaporated to give a residue which was crystallized from acetone/hexane to give 7-(4-methylthiobenzoyl)-2,3-dihydrobenzofuran-5-ylacetic acid, m.p. --150°-152° C.

Workup

  1. temperatureat reflux for approximately 2 hours
  2. temperatureThe reaction mixture was cooled
  3. washwashed with ether
  4. extractionextracted with ethyl acetate
  5. washThe combined organic extracts were washed with water
  6. customevaporated
  7. customto give a residue which
  8. customwas crystallized from acetone/hexane

Sources & evidence

ORD record
ord-130358623f0e4b0e9c58a90821f47127
Source dataset
uspto-grants-1989_03
Patent number
US04816473

Reaction notes

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