Methyl 3-(2-hydroxyethyl)benzoate → 2-Methylpentane

HRID 471008Notes

Reaction equation

HRID 471008 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH:7][CH2:8][CH2:9][C:10]1[CH:11]=[C:12]([CH:17]=[CH:18][CH:19]=1)[C:13](OC)=[O:14]>O1CCCC1>[CH3:13][CH2:12][CH2:11][CH:10]([CH3:19])[CH3:9].[OH:14][CH2:13][C:12]1[CH:11]=[C:10]([CH2:9][CH2:8][OH:7])[CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 2

HCID 10535371Methyl 3-(2-hydroxyethyl)benzoateHCID 21226445Aluminium lithium hydride

Product 2

HCID 78922-MethylpentaneHCID 579891802-(3-(Hydroxymethyl)phenyl)ethanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Lithium aluminum hydride (1M in diethyl ether, 5.55 mL) was added dropwise over 5 min to a stirred solution of methyl 3-(2-hydroxyethyl)benzoate (1.0 g) in tetrahydrofuran (15 mL) cooled in an ice bath. After 1 h, the reaction mixture was quenched with methanol and evaporated in vacuo. Purification was by silica gel chromatography eluting with ethyl acetate:isohexane, 2:1, then ethyl acetate to give the subtitled compound as a gum. Yield 0.5 g.

Workup

  1. temperaturecooled in an ice bath
  2. customthe reaction mixture was quenched with methanol
  3. customevaporated in vacuo
  4. customPurification
  5. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-72fa00a451f64cdcb4b4147b37c97ab2
Source dataset
uspto-grants-2014_01
Patent number
US08629271B2

Reaction notes

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