4-Methoxy-3-propoxybenzaldehyde → (4-Methoxy-3-propoxyphenyl)methanol

HRID 1835298Notes

Reaction equation

HRID 1835298 reaction equation
[CH2:1]([O:4][C:5]1[CH:6]=[C:7]([CH:10]=[CH:11][C:12]=1[O:13][CH3:14])[CH:8]=[O:9])[CH2:2][CH3:3].[BH4-].[Na+]>CCO>[CH2:1]([O:4][C:5]1[CH:6]=[C:7]([CH:10]=[CH:11][C:12]=1[O:13][CH3:14])[CH2:8][OH:9])[CH2:2][CH3:3]

Participants

4

Reactant 2

HCID 5921094-Methoxy-3-propoxybenzaldehydeHCID 4311764Sodium borohydride

Product 1

HCID 28562459(4-Methoxy-3-propoxyphenyl)methanolYield 89%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

Crude 3-(propyloxy)-4-methoxybenzaldehyde (2.60 g) was dissolved in EtOH (30 mL) and cooled to 0° C. NaBH4 (0.499 g, 13.2 mmol) was added portionwise. After the addition was completed, the ice-water bath was removed and the reaction mixture was stirred at room temperature for 2 hours. Water (50 mL) was added and the resulting mixture was extracted with diethyl ether (3×100 mL). The combined organic layers were dried over anhydrous MgSO4. Removal of the solvent gave a pale yellow oil which was purified by silica gel column chromatography (hexanes/EtOAc, 4:1) to give 3-(propyloxy)-4-methoxybenzyl alcohol (2.29 g, 89% over two steps) as a colorless oil.

Workup

  1. additionAfter the addition
  2. customthe ice-water bath was removed
  3. additionWater (50 mL) was added
  4. extractionthe resulting mixture was extracted with diethyl ether (3×100 mL)
  5. dry with materialThe combined organic layers were dried over anhydrous MgSO4
  6. customRemoval of the solvent
  7. customgave a pale yellow oil which
  8. customwas purified by silica gel column chromatography (hexanes/EtOAc, 4:1)

Sources & evidence

ORD record
ord-89d5a2bd1f4c4a28a44d43299de7878e
Source dataset
uspto-grants-2004_08
Patent number
US06770658B2

Reaction notes

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