Benzaldehyde → 4-(5-Phenoxypentyl)benzyl alcohol

HRID 258412Notes

Reaction equation

HRID 258412 reaction equation
[O:1]([CH2:8][CH2:9][CH2:10][C:11]#[C:12][C:13]1[CH:20]=[CH:19][C:16]([CH2:17][OH:18])=[CH:15][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)C1C=CC=CC=1.[BH4-].[Na+].O>C(O)C.OS(O)(=O)=O.C(OCC)(=O)C>[O:1]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]1[CH:14]=[CH:15][C:16]([CH2:17][OH:18])=[CH:19][CH:20]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

8

Reactant 4

HCID 240BenzaldehydeHCID 962WaterHCID 4311764Sodium borohydrideHCID 145767814-(5-Phenoxypent-1-ynyl)benzyl alcohol

Product 1

HCID 145767824-(5-Phenoxypentyl)benzyl alcoholYield 99%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 1118Sulfuric AcidSolventHCID 8857Ethyl AcetateSolvent

Procedure

4-(5-Phenoxypent-1-ynyl)benzyl alcohol--To a solution of 2.02 g of 4-5-phenoxypent-1-ynyl)benzaldehyde (from step (2) above) in 50 mL ethanol at 0° C. was added 640 mg sodium borohydride. After stirring for 1 hour, then addition of 8 mL water and evaporation of the solvents in vacuo, the residue was diluted with 2% H2SO4 and ethyl acetate. The organic layer was washed with brine and saturated NaHCO3 and then dried and the solvent evaporated in vacuo to give the title compound (99%).

Workup

  1. washThe organic layer was washed with brine and saturated NaHCO3
  2. customdried
  3. customthe solvent evaporated in vacuo

Sources & evidence

ORD record
ord-3025a1c049d14277abbf116508c1d341
Source dataset
uspto-grants-1993_11
Patent number
US05266713

Reaction notes

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