Benzenepropanoic acid, 3,5-bis(1,1-dimethylethyl)-4-hydroxy-, ethyl ester → gamma-Propanol

HRID 1165535

Reaction equation

HRID 1165535 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][C:8]([C:11]1[CH:12]=[C:13]([CH2:22][CH2:23][C:24](OCC)=[O:25])[CH:14]=[C:15]([C:18]([CH3:21])([CH3:20])[CH3:19])[C:16]=1[OH:17])([CH3:10])[CH3:9]>C(OCC)C>[CH3:21][C:18]([C:15]1[CH:14]=[C:13]([CH2:22][CH2:23][CH2:24][OH:25])[CH:12]=[C:11]([C:8]([CH3:9])([CH3:7])[CH3:10])[C:16]=1[OH:17])([CH3:19])[CH3:20]

Participants

4

Reactant 2

HCID 64871Benzenepropanoic acid, 3,5-bis(1,1-dimethylethyl)-4-hydroxy-, ethyl esterHCID 21226445Aluminium lithium hydride

Product 1

HCID 169766gamma-PropanolYield 92.7%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a suspension lithium aluminum hydride (11.2 g) in diethyl ether (500 mL) is added over a period of 30 minutes ethyl 3-[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]propionate (60.0 g) in diethyl ether (100 mL). The mixture is heated at reflux for 3 hours and then quenched by the sequential addition of water (11 mL), 10% aqueous sodium hydroxide (11 mL) and water (66 mL). The resulting suspension is washed with tetrahydrofuran and the filtrate is concentrated to give 48 g of 3-[3,5-bis(1,1-dimethylethyl)-4-hydroxy-phenyl]propanol. Trituration of the residue with heptane gave 46 g of light yellow crystals. The 1H NMR spectrum and field desorption mass spectrum are consistent with the above-specified product.

Workup

  1. temperatureThe mixture is heated
  2. temperatureat reflux for 3 hours
  3. customquenched by the sequential addition of water (11 mL), 10% aqueous sodium hydroxide (11 mL) and water (66 mL)
  4. washThe resulting suspension is washed with tetrahydrofuran
  5. concentrationthe filtrate is concentrated

Sources & evidence

ORD record
ord-3995a8fcdfb2460da415e3bbf07a5cfc
Source dataset
uspto-grants-1990_03
Patent number
US04910286

Linked notes

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