1H-Indene-1-carboxylic acid, 2,3-dihydro- → 1-Indanmethanol

HRID 2270074Notes

Reaction equation

HRID 2270074 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[Al+3].[Cl-].[Cl-].[Cl-].[CH:11]1([C:20](O)=[O:21])[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH2:13][CH2:12]1>C(OCC)C.O1CCCC1>[CH:11]1([CH2:20][OH:21])[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH2:13][CH2:12]1

Participants

6

Reactant 3

HCID 857281H-Indene-1-carboxylic acid, 2,3-dihydro-HCID 6451240Aluminum(III) ChlorideHCID 21226445Aluminium lithium hydride

Product 1

HCID 2718801-IndanmethanolYield 74.4%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of LiAlH4 (4.7 g) in diethyl ether (200 ml) was added dropwise a solution of AlCl3 in diethyl ether (200 ml). A solution of 1-indanecarboxylic acid (10 g) (prepared according to the method of Hansen et al. Helv. Chim. Acta 1982, 33, 325-343) in dry tetrahydrofuran (200 ml) was added dropwise at 10-15° C. The mixture was finally stirred at room temperature for 1.5 hours. Excess AlH3 was destroyed by addition of concentrated aqueous NaOH solution (25 ml) at 0° C. Precipitated inorganic salts were filtered off and the solvents evaporated in vacuo leaving 6.8 g of the title compound 1a as a viscous oil which was used without further purification.

Workup

  1. customExcess AlH3 was destroyed by addition of concentrated aqueous NaOH solution (25 ml) at 0° C
  2. customPrecipitated inorganic salts
  3. filtrationwere filtered off
  4. customthe solvents evaporated in vacuo

Sources & evidence

ORD record
ord-684cbecae7f7467db6a5a55c3aa1bd63
Source dataset
uspto-grants-2001_12
Patent number
US06331544B1

Reaction notes

Loading…