Sodium borohydride → HCID 20230520, compound

HRID 2290822Notes

Reaction equation

HRID 2290822 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH2:9][CH2:10][CH2:11][CH2:12][C:13](=[O:19])[CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[CH:5]=[CH:6][C:7]=1[OH:8].[BH4-].[Na+]>CO>[OH:1][C:2]1[CH:3]=[C:4]([CH2:9][CH2:10][CH2:11][CH2:12][CH:13]([OH:19])[CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[CH:5]=[CH:6][C:7]=1[OH:8]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 13519328HCID 13519328, compound

Product 1

HCID 20230520HCID 20230520, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In 1.5 ml of methanol was dissolved 150 mg of 1-(3,4-dihydroxyphenyl)-5-decanone and 20 mg of sodium borohydride was added to the solution under ice-cooling followed by stirring for 30 minutes. Then, the solvent was distilled off from the reaction mixture and after adding 10 ml of water to the residue thus formed, the product was extracted with ether. The extract was dried over anhydrous magnesium sulfate and the solvent was distilled off to provide white crystals of 1-(3,4-dihydroxyphenyl)-5-decanol, which was collected by filtration with the addition of n-hexane. Yield 117 mg.

Workup

  1. additionwas added to the solution under ice-
  2. temperaturecooling
  3. distillationThen, the solvent was distilled off from the reaction mixture
  4. additionafter adding 10 ml of water to the residue
  5. customthus formed
  6. extractionthe product was extracted with ether
  7. dry with materialThe extract was dried over anhydrous magnesium sulfate
  8. distillationthe solvent was distilled off

Sources & evidence

ORD record
ord-6188c5b9730b4ef6b0366206f2f3b3b1
Source dataset
uspto-grants-1986_10
Patent number
US04618627

Reaction notes

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