Methanol → HCID 131715007, compound

HRID 979825Notes

Reaction equation

HRID 979825 reaction equation
[NH2:1][C:2]1[C:3]([Cl:17])=[C:4]2[C:9](=[C:10]([CH3:13])[C:11]=1[Cl:12])[CH:8]([C:14]([OH:16])=[O:15])[CH2:7][CH2:6][CH2:5]2.S(=O)(=O)(O)O.[CH3:23]O>C1C=CC=CC=1>[NH2:1][C:2]1[C:3]([Cl:17])=[C:4]2[C:9](=[C:10]([CH3:13])[C:11]=1[Cl:12])[CH:8]([C:14]([O:16][CH3:23])=[O:15])[CH2:7][CH2:6][CH2:5]2

Participants

5

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 20223041HCID 20223041, compound

Product 1

HCID 131715007HCID 131715007, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

The product from Example 135 (0.5 g) was dissolved in methanol (50 ml) and concentrated sulfuric acid (3 ml) was added. The reaction was refluxed for 4 hours and solvent was evaporated to one-half the volume. The concentrated reaction mixture was diluted with benzene (50 ml) and washed with brine, and aqueous sodium bicarbonate. The organic layer was separated, dried and evaporated affording the desired ester in 89% yield.

Workup

  1. temperatureThe reaction was refluxed for 4 hours
  2. customsolvent was evaporated to one-half the volume
  3. customThe concentrated reaction mixture
  4. washwashed with brine, and aqueous sodium bicarbonate
  5. customThe organic layer was separated
  6. customdried
  7. customevaporated

Sources & evidence

ORD record
ord-333cc66e90d745038706a08c99688756
Source dataset
uspto-grants-1987_01
Patent number
US04634705

Reaction notes

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