Methyl 4-(4-hydroxybutyl)benzoate → 4-(4-Hydroxymethyl-phenyl)-butan-1-ol

HRID 1723982Notes

Reaction equation

HRID 1723982 reaction equation
C[O:2][C:3](=O)[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][CH2:12][CH2:13][OH:14])=[CH:6][CH:5]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[OH:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][CH2:12][CH2:13][OH:14])=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 14603109Methyl 4-(4-hydroxybutyl)benzoateHCID 21226445Aluminium lithium hydride

Product 1

HCID 177561734-(4-Hydroxymethyl-phenyl)-butan-1-olYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirring solution of 4-(4-hydroxy-butyl)-benzoic acid methyl ester (2.24 g, 0.01 mol) in THF (100 mL) was added dropwise a solution of lithium aluminum hydride (8.0 mL, 1M in THF). After completion of addition the reaction mixture continued to stir at room temperature. After 6 hours, the reaction mixture was quenched with water. The aqueous layer was extracted with ethyl acetate. All combined organic layers were dried over Na2SO4, filtered, and concentrated to yield 4-(4-hydroxymethyl-phenyl)-butan-1-ol as a yellow oil (1.90 g, 0.01 mol, 98% yield). 1H (CDCl3, 600 MHz): δ 7.29 (2H, d, J=8.1 Hz), 7.16 (2H, d, J=8.1 Hz), 4.60 (2H, s), 3.60 (2H, t, J=7.5 Hz), 2.62 (2H, t, J=7.5 Hz), 1.67 (2H, m), 1.56 (2H, m); 13C (CDCl3, 150 MHz): δ 141.7, 138.5, 128.5, 127.0, 65.0, 62.5, 35.2, 32.1, 27.5.

Workup

  1. additionAfter completion of addition the reaction mixture
  2. customthe reaction mixture was quenched with water
  3. extractionThe aqueous layer was extracted with ethyl acetate
  4. dry with materialwere dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-44a8473dcc514449b8c4119121d1da04
Source dataset
uspto-grants-2009_02
Patent number
US07485283B2

Reaction notes

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