Sodium Hydroxide → 2,3-dihydro-2,2-diMethylbenzofuran-5-carboxylic acid

HRID 2407474Notes

Reaction equation

HRID 2407474 reaction equation
[OH-].[Na+].C([O:5][C:6]([C:8]1[CH:9]=[CH:10][C:11]2[O:15][C:14]([CH3:17])([CH3:16])[CH2:13][C:12]=2[CH:18]=1)=[O:7])C>>[CH3:16][C:14]1([CH3:17])[CH2:13][C:12]2[CH:18]=[C:8]([C:6]([OH:7])=[O:5])[CH:9]=[CH:10][C:11]=2[O:15]1

Participants

3

Reactant 2

HCID 14798Sodium HydroxideHCID 59509487HCID 59509487, compound

Product 1

HCID 148382312,3-dihydro-2,2-diMethylbenzofuran-5-carboxylic acid

Conditions

Temperature
75 °C

Procedure

An aqueous solution (10 mL) of sodium hydroxide (0.78 g, 0.0195 mol) is added to an ethanolic solution (30 mL) of 2,2-dimethyl-2,3-dihydrobenzofuran-5-carboxylic acid ethyl ester (3.9 g, 0.018 mol). The reaction mixture is heated at 75° C. for four and an half hours. Ethanol is removed under reduced pressure. Demineralized water is added to the residue and pH is brought to ˜3 with 1 N HCl. Solid thus obtained is filtered, washed with demineralized water and dried under reduced pressure to give 2,2-dimethyl-2,3-dihydrobenzofuran-5-carboxylic acid.

Workup

  1. customEthanol is removed under reduced pressure
  2. additionDemineralized water is added to the residue and pH
  3. customSolid thus obtained
  4. filtrationis filtered
  5. washwashed with demineralized water
  6. customdried under reduced pressure

Sources & evidence

ORD record
ord-a00a28ebb39b4582afdeb63a8db86b20
Source dataset
uspto-grants-2014_08
Patent number
US08809539B2

Reaction notes

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