Sodium Hydroxide → (2,3-Dihydrobenzofuran-6-yl)methanol

HRID 869867Notes

Reaction equation

HRID 869867 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[O:7]1[C:11]2[CH:12]=[C:13]([C:16](OC)=[O:17])[CH:14]=[CH:15][C:10]=2[CH2:9][CH2:8]1.[OH-].[Na+]>C1COCC1>[O:7]1[C:11]2[CH:12]=[C:13]([CH2:16][OH:17])[CH:14]=[CH:15][C:10]=2[CH2:9][CH2:8]1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 59942373Methyl 2,3-dihydro-1-benzofuran-6-carboxylate

Product 1

HCID 18356898(2,3-Dihydrobenzofuran-6-yl)methanolYield 92%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred solution of lithium aluminium hydride (6.1 g, 250 mmol) in THF (300 mL) was added a solution of methyl 2,3-dihydrobenzofuran-6-carboxylate (17.8 g, 100 mmol) in THF at 0□. The mixture was stirred at room temperature for 1 h. A saturated aqueous NaOH solution was added and the mixture was extracted with ethyl acetate. The combined organic layers were washed with brine and dried over Na2SO4, filtered and concentrated to afford (2,3-dihydrobenzofuran-6-yl)methanol (13.8 g, 92.0% yield). 1H NMR (400 MHz, CDCl3) δ: 7.17 (d, J=7.2, 1H), 6.84 (d, J=7.2, 1H), 6.81 (s, 1H), 4.62 (s, 2H), 4.58 (t, J=8.4, 2H), 3.20 (t, J=8.4, 2H),) 1.67 (br s, 1H).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-9a98ba94ec504febbe4ff57fcb5e3ecf
Source dataset
uspto-grants-2015_03
Patent number
US08969386B2

Reaction notes

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