Water → 2-(2,3-Dihydro-1H-inden-1-yl)ethan-1-ol

HRID 480294Notes

Reaction equation

HRID 480294 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH:7]1([CH2:16][C:17](O)=[O:18])[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH2:9][CH2:8]1.O.CCOC(C)=O>CCOCC>[CH:7]1([CH2:16][CH2:17][OH:18])[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH2:9][CH2:8]1

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 965011-Indanylacetic acidHCID 21226445Aluminium lithium hydride

Product 1

HCID 123228632-(2,3-Dihydro-1H-inden-1-yl)ethan-1-olYield 92.5%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Lithium aluminum hydride (1 M in Et2O, 14 mL, 14 mmol) was slowly added to a solution of 2-indanylacetic acid (2.5 g, 14 mmol) in Et2O. The reaction mixture was heated at reflux for 2 h and was cooled to room temperature. Water and EtOAc were added and the organic solution was washed with water (2×) and brine (1×), dried over MgSO4, filtered, and concentrated to afford 2-indanylethanol (2.1 g) which was used in the next step without further purification. 1H NMR (400 MHz, CDCl3) δ 7.08-7.24 (m, 4H), 3.75 (t, 2H), 3.07 (m, 2H), 2.61 (m, 3H), 1.80 (m, 2H); MS 180 (M+18).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 2 h
  3. washthe organic solution was washed with water (2×) and brine (1×)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-ae2fe725b6c448ad99c9abee24b22c52
Source dataset
uspto-grants-2003_11
Patent number
US06649657B2

Reaction notes

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