Hexane → (3-Butoxy-5-hydroxymethyl-phenyl)-methanol

HRID 2261809Notes

Reaction equation

HRID 2261809 reaction equation
C[O:2][C:3](=O)[C:4]1[CH:12]=[C:11]([O:13][CH2:14][CH2:15][CH2:16][CH3:17])[CH:10]=[C:6]([C:7](O)=[O:8])[CH:5]=1.CCCCCC>C1COCC1>[CH2:14]([O:13][C:11]1[CH:10]=[C:6]([CH2:7][OH:8])[CH:5]=[C:4]([CH2:3][OH:2])[CH:12]=1)[CH2:15][CH2:16][CH3:17]

Participants

4

Reactant 2

HCID 8058HexaneHCID 67528487HCID 67528487, compound

Product 1

HCID 57443335(3-Butoxy-5-hydroxymethyl-phenyl)-methanolYield 92.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 5-Butoxy-isophthalic acid monomethyl ester (1.0 g, 4.0 mmol) in THF (20 mL) is treated with 2.0 M borane-dimethyl sulfide complex in hexane (10 mL, 20 mmol). The mixture is stirred at room temperature for 48 h. The mixture is quenched carefully with methanol (10 mL) and is concentrated to dryness. The residue is purified by flash chromatography to afford the title compound as a solid (0.78 g, 88%). LC-ES/MS m/e 211.3 (M+1).

Workup

  1. customThe mixture is quenched carefully with methanol (10 mL)
  2. concentrationis concentrated to dryness
  3. customThe residue is purified by flash chromatography

Sources & evidence

ORD record
ord-4f7d6df673294532b8f7171ae1668756
Source dataset
uspto-grants-2010_12
Patent number
US07846960B2

Reaction notes

Loading…