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

HRID 2382545Notes

Reaction equation

HRID 2382545 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-f6c36892621a41608883d5b02a7fff32
Source dataset
uspto-grants-2012_09
Patent number
US08263042B2

Reaction notes

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