Hydrochloric Acid → 3-((E)-Hex-2-enyl)-3-methyl-2,3-dihydro-benzofuran-6-carboxylic acid

HRID 2092991Notes

Reaction equation

HRID 2092991 reaction equation
C[O:2][C:3]([C:5]1[CH:20]=[CH:19][C:8]2[C:9]([CH2:13]/[CH:14]=[CH:15]/[CH2:16][CH2:17][CH3:18])([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:19]=[CH:20][C:5]([C:3]([OH:4])=[O:2])=[CH:6][C:7]=2[O:11][CH2:10]1)/[CH:14]=[CH:15]/[CH2:16][CH2:17][CH3:18]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 14798Sodium HydroxideHCID 684812333-((E)-Hex-2-enyl)-3-methyl-2,3-dihydro-benzofuran-6-carboxylic acid methyl ester

Product 1

HCID 684796473-((E)-Hex-2-enyl)-3-methyl-2,3-dihydro-benzofuran-6-carboxylic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 3-((E)-Hex-2-enyl)-3-methyl-2,3-dihydro-benzofuran-6-carboxylic acid methyl ester (200 mg, 0.73 mmol), sodium hydroxide (200 mg, 5 mmol), ethanol (7 ml) and water (1 ml) in tetrahydrofuran (7 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 colorless oil which crystallized (M: 155 mg, 82%).

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 colorless oil which
  6. customcrystallized (M: 155 mg, 82%)

Sources & evidence

ORD record
ord-9d5a2394990a4b919572dbcd814ce85d
Source dataset
uspto-grants-2013_05
Patent number
US08440832B2

Reaction notes

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