Hydrochloric Acid → HCID 14257795, compound

HRID 2292059Notes

Reaction equation

HRID 2292059 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 Preparation 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-26be39bef9e74b03bee0fd548254f20c
Source dataset
uspto-grants-1989_01
Patent number
US04800228

Reaction notes

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