Sodium borohydride → 3,5-Dimethyl-4-(3'-iso-propyl-4'-methoxyphenoxy)benzyl alcohol

HRID 1170986Notes

Reaction equation

HRID 1170986 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([CH3:22])[C:9]=1[O:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[C:13]([CH:19]([CH3:21])[CH3:20])[CH:12]=1)[CH:5]=[O:6].[BH4-].[Na+]>CO>[CH3:22][C:8]1[CH:7]=[C:4]([CH:3]=[C:2]([CH3:1])[C:9]=1[O:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[C:13]([CH:19]([CH3:20])[CH3:21])[CH:12]=1)[CH2:5][OH:6]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 222856654-(3-Isopropyl-4-methoxy-phenoxy)-3,5-dimethyl-benzaldehyde

Product 1

HCID 251506013,5-Dimethyl-4-(3'-iso-propyl-4'-methoxyphenoxy)benzyl alcoholYield 83%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of 3,5-dimethyl-4-(3′-iso-propyl-4′-methoxyphenoxy)benzaldehyde (4.1 g, 15.2 mmol, Example 28, step a) in methanol (35 mL) at 0° C. was slowly added NaBH4 (1.16 g, 30.5 mmol). The reaction mixture was stirred at room temperature for 5 h and the solvent was removed under reduced pressure. The residue was dissolved in ethyl acetate (150 mL), washed with brine, dried over Na2SO4 and concentrated under reduced pressure. The crude product was purified by column chromatography on silica gel, eluting with ethyl acetate-hexanes (2:4) to afford 3,5-dimethyl-4-(3′-iso-propyl-4′-methoxyphenoxy)benzyl alcohol as a white solid (3.4 g, 83%, m.p.: 78-80° C.): 1H NMR (300 MHz, CDCl3): δ 7.12 (s, 2 H), 6.80 (d, J=3.3 Hz, 2 H), 6.67 (d, J=9.0 Hz, 1 H), 6.36 (dd, J=3.0, 8.7 Hz, 1 H), 4.68 (s, 2 H), 3.80 (s, 3 H), 3.35-3.25 (m, 1 H), 2.16 (s, 6 H), 1.19 (d, J=7.2 Hz, 6 H); TLC conditions: Uniplate silica gel, 250 microns; mobile phase=ethyl acetate-hexanes (2:4); Rf=0.5.

Workup

  1. customat 0° C.
  2. customthe solvent was removed under reduced pressure
  3. dissolutionThe residue was dissolved in ethyl acetate (150 mL)
  4. washwashed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated under reduced pressure
  7. customThe crude product was purified by column chromatography on silica gel
  8. washeluting with ethyl acetate-hexanes (2:4)

Sources & evidence

ORD record
ord-9122d9bc817c4f329b1925b6e9c083a6
Source dataset
uspto-grants-2010_11
Patent number
US07829552B2

Reaction notes

Loading…