Hydrochloric Acid → HCID 18433874, compound

HRID 2305949Notes

Reaction equation

HRID 2305949 reaction equation
[CH:1]1([CH:6]([CH3:12])[CH2:7][CH2:8][CH2:9][CH:10]=[O:11])[CH2:5][CH2:4][CH2:3][CH2:2]1.[BH4-].[Na+].Cl>C(O)C.CC(OC)(C)C>[CH:1]1([CH:6]([CH3:12])[CH2:7][CH2:8][CH2:9][CH2:10][OH:11])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 18433870HCID 18433870, compound

Product 1

HCID 18433874HCID 18433874, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 15413tert-Butyl methyl etherSolvent

Procedure

5-Cyclopentylhexanal (4.2 g; 25 mmol) in ethanol (40 ml) was added to sodium borohydride (1.2 g; 32 mmol) suspended in the same solvent (50 ml) at 10° C. The reaction mixture was stirred at room temperature for 2 hours and then 1 N HCl (50 ml) was added dropwise at 0° C. The mixture was diluted with MTBE (150 ml), the organic layer separated, washed with brine (3×250 ml), dried (MgSO4), concentrated in vacuo, and bulb-to-bulb distilled (125° C./0.2 torr) to give 3.4 g (80% yield) of 5-cyclopentylhexan-1-ol.

Workup

  1. customthe organic layer separated
  2. washwashed with brine (3×250 ml)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo, and bulb-to-bulb
  5. distillationdistilled (125° C./0.2 torr)

Sources & evidence

ORD record
ord-c6364ba4499b4e5d9443152d149a3ade
Source dataset
uspto-grants-2002_08
Patent number
US06441052B1

Reaction notes

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