Ethyl 3-phenylindan-1-acetate → 2-(3-Phenylindan-1-yl)ethanol

HRID 1389825Notes

Reaction equation

HRID 1389825 reaction equation
[C:1]1([CH:7]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[CH:9]([CH2:16][C:17](OCC)=[O:18])[CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[C:1]1([CH:7]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[CH:9]([CH2:16][CH2:17][OH:18])[CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 12565675Ethyl 3-phenylindan-1-acetateHCID 21226445Aluminium lithium hydride

Product 1

HCID 125656762-(3-Phenylindan-1-yl)ethanolYield 66.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
80 °C

Procedure

Ethyl 3-phenylindan-1-acetate (84.3 g, 0.3 mol) in THF (300 ml) was added dropwise with stirring to LiAlH4 (10 g) in THF (200 ml) under N2 and the mixture stirred at 80° C. overnight. Processing by standard conditions yielded 2-(3-phenylindan-1-yl)ethanol as an oil (47.3 g), IR 3100-3600 cm-1 (OH). This alcohol could also obtained by reduction of the ester in THF using LiBH4. The alcohol (43.15 g, 0.18 mol) was refluxed overnight with 48% HBr (280 ml), cooled, extracted with ether which, with standard processing, gave 2-(3-phenylindan-1-yl) ethyl bromide (50.8 g) as an oil. This bromo-compound (41.8 g, 0.14 mol) in Me2CO (160 ml) was added to a solution of NaCN (7 g, 0.143 mol) in H2O (40 ml) and the solution stirred and refluxed for 64 hours. The solution was evaporated to dryness and the product extracted with a mixture of AcOEt and H2O. After drying (Na2SO4), filtration and evaporation 3-(3-phenylindan-1-yl)propionitrile (26.8 g) was obtained as a solid, IR 2250 cm-1 (CN). This nitrile (24.3 g, 0.1 mol) in hot EtOCH2CH2OH (100 ml) was treated with NaOH (24.3 g, 0.6 mol) in H2O (40 ml) and the solution refluxed for 6 hours. It was then poured into conc. HCl (50 ml) in H2O (250 ml), extracted with Et2O and the Et2O extracted with 2N NaOH. Acidification gave the title compound. NMR (CCl4)δ1.5-3.3 (7H, CH2), 4.12 (1H, CH), 6.8-7.3 (9H,Ar), 11.92 (1H, exchangeable). cl EXAMPLE 3

Sources & evidence

ORD record
ord-b7c418dd27da4f3798226a0121742280
Source dataset
uspto-grants-1981_01
Patent number
US04246281

Reaction notes

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