Hydrochloric Acid → HCID 14257795, compound

HRID 868256Notes

Reaction equation

HRID 868256 reaction equation
[OH:1][C:2]1[C:10]2[O:9][C:8]([C:11]([O:13]CC)=[O:12])=[C:7]([CH3:16])[C:6]=2[CH:5]=[C:4]([CH3:17])[C:3]=1[CH3:18].[OH-].[Na+].Cl>CO.C1COCC1>[OH:1][C:2]1[C:10]2[O:9][C:8]([C:11]([OH:13])=[O:12])=[C:7]([CH3:16])[C:6]=2[CH:5]=[C:4]([CH3:17])[C:3]=1[CH3:18]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 14257794HCID 14257794, compound

Product 1

HCID 14257795HCID 14257795, compound

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Ethyl 7-hydroxy-3,5,6-trimethylbenzofuran-2-carboxylate (90 g, 0.37 mole) (from Example 2, Step 3) was dissolved in 1:1 MeOH/THF (600 mL) and cooled to 0° C. Dropwise addition of 2N NaOH (750 mL) followed by warming to room temperature for a 2 hr period effected saponification of the ester. The reaction was acidified with conc. HCl (150 mL) and the product extracted into EtOAc, dried (Na2SO4) and the solvent evaporated to give the carboxylic acid used directly in the next step.

Workup

  1. temperatureby warming to room temperature for a 2 hr period
  2. extractionthe product extracted into EtOAc
  3. dry with materialdried (Na2SO4)
  4. customthe solvent evaporated

Sources & evidence

ORD record
ord-784e5326496742a483255e9955bc5afa
Source dataset
uspto-grants-1988_10
Patent number
US04778805

Reaction notes

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