Diethyl Ether → Pentadecan-2-ol

HRID 1950692Notes

Reaction equation

HRID 1950692 reaction equation
[CH3:1][C:2](=[O:16])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15].C(OCC)C.[BH4-].[Na+]>C1(C)C=CC=CC=1>[CH3:1][CH:2]([OH:16])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 613032-PentadecanoneHCID 4311764Sodium borohydride

Product 1

HCID 96687Pentadecan-2-ol

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Pentadecanone (200 g) was added a 3-litre three-necked flask under nitrogen, to which diethyl ether (1000 ml) was slowly added from a dropping funnel. Sodium borohydride (63.54 g) was then slowly added and the mixture stirred for two days at room temperature under nitrogen. Toluene was added to the reaction vessel and the contents transferred to a separating funnel. The organic layer was washed with water and the aqueous layer was collected. The aqueous layer was washed with toluene, which was combined with the previous organic layer. The product was dried with magnesium sulphate and filtered under vacuum. The solvent was then stripped on a rotary evaporator at 100° C. to yield the title compound.

Workup

  1. customthe contents transferred to a separating funnel
  2. washThe organic layer was washed with water
  3. customthe aqueous layer was collected
  4. washThe aqueous layer was washed with toluene, which
  5. dry with materialThe product was dried with magnesium sulphate
  6. filtrationfiltered under vacuum
  7. customThe solvent was then stripped on a rotary evaporator at 100° C.

Sources & evidence

ORD record
ord-6ea66d273ef341f6b1f0fb276b674f02
Source dataset
uspto-grants-2013_03
Patent number
US08404627B2

Reaction notes

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