Sodium Hydroxide → HCID 18690805, compound

HRID 1871253Notes

Reaction equation

HRID 1871253 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[C:7]([C:11]1[CH:19]=[C:18]2[C:14]([CH2:15][CH2:16][CH:17]2[CH2:20][C:21](OC)=[O:22])=[CH:13][CH:12]=1)([CH3:10])([CH3:9])[CH3:8].[OH-].[Na+]>CCOCC>[C:7]([C:11]1[CH:19]=[C:18]2[C:14]([CH2:15][CH2:16][CH:17]2[CH2:20][CH2:21][OH:22])=[CH:13][CH:12]=1)([CH3:10])([CH3:8])[CH3:9]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 54247785HCID 54247785, compound

Product 1

HCID 18690805HCID 18690805, compoundYield 112.3%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a suspension of 1.72 g of LiAlH4 (45.03 mmole) in 100 ml of ether was added dropwise a solution of 10.7 g of methyl 6-tert-butyl-1-indanacetate (36.9 mmole) dissolved in 50 ml of ether. After refluxing the suspension during 2 h, 8.6 ml of 1 N NaOH were carefully added and, after 1 h, the suspension was filtered and concentrated to give 9.05 g of raw 2-(6tert-butyl-1-indanyl)-1-ethanol 78.1% pure. Bulb-to-bulb distillation (150°/20 Pa) provided 8.53 g of 2-(6-tert-butyl-1-indanyl)-1-ethanol with a GC purity of 82.3%. Yield of the last three steps: 71.0%.

Workup

  1. temperatureAfter refluxing the suspension during 2 h
  2. filtrationthe suspension was filtered
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-78512098a0aa4a34875d3625e3e9bb1f
Source dataset
uspto-grants-2000_08
Patent number
US06103688

Reaction notes

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