Dimethyl 5-butoxyisophthalate → (3-Butoxy-5-hydroxymethyl-phenyl)-methanol

HRID 58976Notes

Reaction equation

HRID 58976 reaction equation
[CH2:1]([O:5][C:6]1[CH:7]=[C:8]([C:16](OC)=[O:17])[CH:9]=[C:10]([CH:15]=1)[C:11](OC)=[O:12])[CH2:2][CH2:3][CH3:4].[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[CH2:1]([O:5][C:6]1[CH:15]=[C:10]([CH2:11][OH:12])[CH:9]=[C:8]([CH2:16][OH:17])[CH:7]=1)[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 18667930Dimethyl 5-butoxyisophthalateHCID 21226445Aluminium lithium hydride

Product 1

HCID 57443335(3-Butoxy-5-hydroxymethyl-phenyl)-methanolYield 60.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of dimethyl 5-butoxyisophthalate (0.51 g, 1.90 mmol) in THF (16 mL) was slowly added LiAlH4 (0.40 g, 10.5 mmol). The reaction mixture was stirred for 8 h. The reaction was quenched by the addition of 2N aq. HCl (5 mL). The mixture was extracted with Et2O (2×25 mL) and EtOAc (2×25 mL), the organics layers combined, dried over Na2SO4, filtered, and concentrated under reduced pressure to afford the desired product (0.24 g) as an oil, which was used without further purification.

Workup

  1. customThe reaction was quenched by the addition of 2N aq. HCl (5 mL)
  2. extractionThe mixture was extracted with Et2O (2×25 mL) and EtOAc (2×25 mL)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-31b6da7972c84e80a6fc41a44c88dc8c
Source dataset
uspto-grants-2016_09
Patent number
US09439433B2

Reaction notes

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