Ethyl 3-(1,1-dimethylethyl)-4-hydroxy-5-methylbenzenepropanoate → 75546-54-2

HRID 1165536Notes

Reaction equation

HRID 1165536 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][C:8]([C:11]1[CH:12]=[C:13]([CH2:19][CH2:20][C:21](OCC)=[O:22])[CH:14]=[C:15]([CH3:18])[C:16]=1[OH:17])([CH3:10])[CH3:9]>O1CCCC1>[CH3:10][C:8]([C:11]1[CH:12]=[C:13]([CH2:19][CH2:20][CH2:21][OH:22])[CH:14]=[C:15]([CH3:18])[C:16]=1[OH:17])([CH3:7])[CH3:9]

Participants

4

Reactant 2

HCID 19862069Ethyl 3-(1,1-dimethylethyl)-4-hydroxy-5-methylbenzenepropanoateHCID 21226445Aluminium lithium hydride

Product 1

HCID 685085675546-54-2Yield 59.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension lithium aluminum hydride (15.2 g) in tetrahydrofuran (500 mL) is added over a period of 60 minutes ethyl 3-[3-(1,1-dimethylethyl)-4-hydroxy-5-methylphenyl]propionate (80.0 g) in tetrahydrofuran (100 mL). The mixture is heated at reflux for 2 hours and then quenched by the sequential addition of water (17 mL), 10% aqueous sodium hydroxide (17 mL) and water (51 mL). The resulting suspension is washed with tetrahydrofuran and the filtrate is concentrated to give 40 g of crude 3-[3-(1,1-dimethylethyl)-4-hydroxy-5-methylphenyl]propanol. The crude intermediate is crystallized from heptane/toluene to give 38 g of light yellow crystals. The 1H NMR and field desorption spectra are consistent with the above-specified product.

Workup

  1. temperatureThe mixture is heated
  2. temperatureat reflux for 2 hours
  3. customquenched by the sequential addition of water (17 mL), 10% aqueous sodium hydroxide (17 mL) and water (51 mL)
  4. washThe resulting suspension is washed with tetrahydrofuran
  5. concentrationthe filtrate is concentrated

Sources & evidence

ORD record
ord-aaca8c4a726b4307870b2df81f6fa971
Source dataset
uspto-grants-1990_03
Patent number
US04910286

Reaction notes

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