Hydrochloric Acid → 3-Benzyl-3-methyl-2,3-dihydro-benzofuran-6-carboxylic acid

HRID 2092975Notes

Reaction equation

HRID 2092975 reaction equation
C[O:2][C:3]([C:5]1[CH:21]=[CH:20][C:8]2[C:9]([CH2:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)([CH3:12])[CH2:10][O:11][C:7]=2[CH:6]=1)=[O:4].[OH-].[Na+].C(O)C.Cl>O1CCCC1.O>[CH2:13]([C:9]1([CH3:12])[C:8]2[CH:20]=[CH:21][C:5]([C:3]([OH:4])=[O:2])=[CH:6][C:7]=2[O:11][CH2:10]1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 14798Sodium HydroxideHCID 251290463-Benzyl-3-methyl-2,3-dihydro-benzofuran-6-carboxylic acid methyl ester

Product 1

HCID 251290473-Benzyl-3-methyl-2,3-dihydro-benzofuran-6-carboxylic acidYield 105.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 3-Benzyl-3-methyl-2,3-dihydro-benzofuran-6-carboxylic acid methyl ester (300 mg, 1.06 mmol) obtained in Example 4(B), sodium hydroxide (260 mg, 6.5 mmol), ethanol (10 ml) and water (1 ml) in tetrahydrofuran (10 ml), is stirred for 12 h at room temperature. The reaction medium is acidified by adding a 1.2 M hydrochloric acid solution and extracted with ethyl acetate. The organic phase is washed with water, dried (Na2SO4), and concentrated in a rotary evaporator. The product is obtained as a white solid (300 mg, 100%). Mp: 165° C.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic phase is washed with water
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated in a rotary evaporator

Sources & evidence

ORD record
ord-4f57f93e174144a38a2825d3ef270406
Source dataset
uspto-grants-2013_05
Patent number
US08440832B2

Reaction notes

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