Hydrochloric Acid → HCID 54216858, compound

HRID 275178Notes

Reaction equation

HRID 275178 reaction equation
[C:1]([O:4][C:5]1[CH:6]=[C:7]([CH:10]=[CH:11][C:12]=1[O:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[CH:8]=[O:9])(=[O:3])[CH3:2].[BH4-].[Na+].Cl>CO>[C:1]([O:4][C:5]1[CH:6]=[C:7]([CH:10]=[CH:11][C:12]=1[O:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[CH2:8][OH:9])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 200905923-Acetoxy-4-pentyloxy-benzaldehyde

Product 1

HCID 54216858HCID 54216858, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

3-Acetoxy-4-pentyloxy-benzaldehyde (0.75 g., 3.0 mmol, 1 equiv.) is dissolved in 15 mL of MeOH, and the mixture cooled to 0° C. Sodium borohydride (0.230 g., 6 mmol., 2 equiv.) is added in portions. After stirring for 30 min., the mixture is neutralized with 1N HCl, and then extracted thrice with ether. The extracts are washed with brine, dried (MgSO4), and evaporated. Chromatography on silica gel using CH2Cl2 /hexane affords 3-acetoxy-4-pentyloxy-benzyl alcohol (12f) (0.680 g., 2.70 mmol., 90%): mp=35°-36° C.; 1H NMR (300 MHz, CDCl3) δ 7.17 (dd, J=2, 8 Hz, 1H, ArH), 7.05 (d, J=2 Hz, 1H, ArH), 6.92 (d, J=8 Hz, 1H, ArH), 4.85 (s, 1H, OH), 4.60 (s, 2H, ArCH2O), 3.95 (t, J=7 Hz, 2H, OCH2R), 2.30 (s, 3H, CH3CO), 1.75 (m, 2H, OCH2CH2), 1.38 (m, 4H, CH2CH2CH3), 0.90 (t, J=7 Hz, 3H, RCH2CH3).

Workup

  1. extractionextracted thrice with ether
  2. washThe extracts are washed with brine
  3. dry with materialdried (MgSO4)
  4. customevaporated

Sources & evidence

ORD record
ord-aa3c10a639cf41c387fec4dcf678e762
Source dataset
uspto-grants-1995_02
Patent number
US05391817

Reaction notes

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