Methanol → HCID 21545983, compound

HRID 1606104Notes

Reaction equation

HRID 1606104 reaction equation
C(=O)(O)[O-].[Na+].CO.[CH3:8][CH:9]([CH3:29])[CH2:10][CH2:11][O:12][C:13]1[CH:14]=[C:15]2[C:20](=[CH:21][CH:22]=1)[S:19][C:18]([C:23]([O:25]CC)=[O:24])=[CH:17][C:16]2=[O:28]>O>[CH3:8][CH:9]([CH3:29])[CH2:10][CH2:11][O:12][C:13]1[CH:14]=[C:15]2[C:20](=[CH:21][CH:22]=1)[S:19][C:18]([C:23]([OH:25])=[O:24])=[CH:17][C:16]2=[O:28]

Participants

5

Reactant 3

HCID 887MethanolHCID 516892Sodium BicarbonateHCID 21545978HCID 21545978, compound

Product 1

HCID 21545983HCID 21545983, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A mixture of 9 parts of ethyl 6-hydroxy-1-thiachromone-2-carboxylate, 15 parts of isoamyl bromide and 14 parts of anhydrous potassium carbonate in 130 parts of acetone was stirred and heated under reflux for 18 hours. Insoluble material was then filtered off and washed with acetone and the total acetone solution was evaporated to leave a yellow solid, which was crystallized from ethanol to give 4.1 parts of ethyl 6-(3-methylbutoxy)-1-thiachromone-2-carboxylate, melting point 83°-84°C. This entire product was heated under reflux for 2 hours with a solution of 1.5 parts of sodium bicarbonate in 35 parts of water and 25 parts of methanol. The methanol was then boiled off and the solution was diluted with 70 parts of water. The aqueous solution was thoroughly washed with ether, filtered then acidified with concentrated hydrochloric acid. A precipitate was obtained which was filtered off, washed with water and dried, then extracted with boiling benzene. The product was then filtered off and dried to leave 3.95 parts of 6-(3-methylbutoxy)-1-thiachromone-2-carboxylic acid, melting point 208°-209°C.

Workup

  1. temperatureThis entire product was heated
  2. washThe aqueous solution was thoroughly washed with ether
  3. filtrationfiltered
  4. customA precipitate was obtained which
  5. filtrationwas filtered off
  6. washwashed with water
  7. customdried
  8. extractionextracted with boiling benzene
  9. filtrationThe product was then filtered off
  10. customdried

Sources & evidence

ORD record
ord-7e6eea0480364f74a49e033e567213c0
Source dataset
uspto-grants-1976_04
Patent number
US03952013

Reaction notes

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