Hydrochloric Acid → 3-(4-Chloro-benzyl)-3-methyl-2,3-dihydro-benzofuran-6-carboxylic acid

HRID 2092986Notes

Reaction equation

HRID 2092986 reaction equation
C[O:2][C:3]([C:5]1[CH:22]=[CH:21][C:8]2[C:9]([CH2:13][C:14]3[CH:19]=[CH:18][C:17]([Cl:20])=[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>[Cl:20][C:17]1[CH:18]=[CH:19][C:14]([CH2:13][C:9]2([CH3:12])[C:8]3[CH:21]=[CH:22][C:5]([C:3]([OH:4])=[O:2])=[CH:6][C:7]=3[O:11][CH2:10]2)=[CH:15][CH:16]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 14798Sodium HydroxideHCID 684823953-(4-Chloro-benzyl)-3-methyl-2,3-dihydro-benzofuran-6-carboxylic acid methyl ester

Product 1

HCID 684824633-(4-Chloro-benzyl)-3-methyl-2,3-dihydro-benzofuran-6-carboxylic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 3-(4-Chloro-benzyl)-3-methyl-2,3-dihydro-benzofuran-6-carboxylic acid methyl ester (100 mg, 0.32 mmol), sodium hydroxide (100 mg, 2.5 mmol), ethanol (3 ml) and water (0.5 ml) in tetrahydrofuran (4 ml), was stirred for 12 h at room temperature. The reaction medium was acidified by adding a 1.2 M hydrochloric acid solution and extracted with ethyl acetate. The organic phase was washed with water, dried (Na2SO4), and concentrated in a rotary evaporator. The product was obtained as a white solid. (M: 89 mg, 92%).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic phase was washed with water
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated in a rotary evaporator
  5. customThe product was obtained as a white solid

Sources & evidence

ORD record
ord-ff6b56428e5a485482190a35061e80ec
Source dataset
uspto-grants-2013_05
Patent number
US08440832B2

Reaction notes

Loading…