Sodium borohydride → HCID 53828330, compound

HRID 2231857Notes

Reaction equation

HRID 2231857 reaction equation
[BH4-].[Na+].[CH2:3]([C:12]1[CH:19]=[CH:18][CH:17]=[CH:16][C:13]=1[CH:14]=[O:15])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11]>CO>[CH2:3]([C:12]1[CH:19]=[CH:18][CH:17]=[CH:16][C:13]=1[CH2:14][OH:15])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 22222788HCID 22222788, compound

Product 1

HCID 53828330HCID 53828330, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

0.57 g of sodium borohydride is added in portions, over a period of 15 minutes, to a stirred solution of 9.3 g of 2-nonylbenzaldehyde in 150 ml of methanol. After stirring for a further 30 minutes, the reaction mixture is concentrated by evaporation under reduced pressure and the residue is taken up in ether. The organic phase is washed with ice-cooled 0.2N hydrochloric acid and with water, dried over sodium sulphate and concentrated by evaporation in vacuo. Chromatographic purification of the residue on silica gel with mixtures of petroleum ether with an increasing amount of ether yields 2-nonylbenzyl alcohol in the form of a pale yellow oil.

Workup

  1. concentrationthe reaction mixture is concentrated by evaporation under reduced pressure
  2. washThe organic phase is washed with ice-
  3. temperaturecooled 0.2N hydrochloric acid
  4. dry with materialwith water, dried over sodium sulphate
  5. concentrationconcentrated by evaporation in vacuo
  6. customChromatographic purification of the residue on silica gel with mixtures of petroleum ether with an increasing amount of ether

Sources & evidence

ORD record
ord-f5af8f91ec3945008c2b12010aaa5a65
Source dataset
uspto-grants-1988_11
Patent number
US04785004

Reaction notes

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