Hydrochloric Acid → 3,3-Dimethyl-2,3-dihydrobenzofuran-6-carboxylic acid

HRID 1256406Notes

Reaction equation

HRID 1256406 reaction equation
[CH3:1][C:2]1([CH3:15])[C:6]2[CH:7]=[CH:8][C:9]([C:11]([O:13]C)=[O:12])=[CH:10][C:5]=2[O:4][CH2:3]1.[OH-].[Na+].Cl>CO>[CH3:1][C:2]1([CH3:15])[C:6]2[CH:7]=[CH:8][C:9]([C:11]([OH:13])=[O:12])=[CH:10][C:5]=2[O:4][CH2:3]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 58279528Methyl 3,3-dimethyl-2,3-dihydrobenzofuran-6-carboxylate

Product 1

HCID 582795703,3-Dimethyl-2,3-dihydrobenzofuran-6-carboxylic acidYield 77%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In a 50 ml pear flask containing methyl 3,3-dimethyl-2,3-dihydrobenzofuran-6-carboxylate (32 mg, 0.16 mmol) were added methanol (3 ml) and 1.0 M sodium hydroxide (6 ml, 6 mmol) solution to give a suspension. This was stirred at room temperature for 1 hour. Then 2N hydrochloride solution (3.5 ml) was added to neutralize the excess base. The acidic mixture (pH ˜2) was then extracted with EtOAc twice, and the combined organic layers were dried over MgSO4, filtered and concentrated to give the desired 3,3-dimethyl-2,3-dihydrobenzofuran-6-carboxylic acid (23 mg, 77% yield) as a white flakey oily solid that was used in the next step without further purification.

Workup

  1. customto give a suspension
  2. extractionThe acidic mixture (pH ˜2) was then extracted with EtOAc twice
  3. dry with materialthe combined organic layers were dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-e8a66f1012934589926280ec678eda6c
Source dataset
uspto-grants-2013_06
Patent number
US08461163B2

Reaction notes

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