Benzyl Alcohol → 1-(Benzyloxy)decan-2-ol

HRID 1649728Notes

Reaction equation

HRID 1649728 reaction equation
[CH2:1]([OH:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[O:11]1[CH:13]([CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[CH2:12]1.[Na]>CN(C=O)C.O.C(O)(=O)C>[C:2]1([CH2:1][O:8][CH2:12][CH:13]([OH:11])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

8

Reactant 4

HCID 244Benzyl AlcoholHCID 169931,2-EpoxydecaneHCID 24758Sodium hydrideHCID 5360545Sodium

Product 1

HCID 143916241-(Benzyloxy)decan-2-ol

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Conditions

Temperature
80 °C

Procedure

Benzyl alcohol (108 g, 1.0 mol) is added to a suspension of 50% sodium hydride-mineral oil (48 g, 1.0 mol) in DMF (200 ml) at room temperature. The mixture is then heated to 80° C. for two hours. A solution of 1,2-epoxydecane* (85 ml) in DMF (50 ml) is added slowly to the sodium salt over 30 minutes and the mixture is then heated at 80° C. for 20 hours. The reaction mixture is cooled, diluted with water, neutralized with acetic acid, and extracted with ether. The ether extract is concentrated to give an oil which is distilled to give the desired product (131 g), bp 178°-180° C./4 mm.

Workup

  1. temperaturethe mixture is then heated at 80° C. for 20 hours
  2. temperatureThe reaction mixture is cooled
  3. extractionextracted with ether
  4. extractionThe ether extract
  5. concentrationis concentrated
  6. customto give an oil which
  7. distillationis distilled

Sources & evidence

ORD record
ord-407b087f9d3d4be9aa6984f542cea006
Source dataset
uspto-grants-1990_05
Patent number
US04921859

Reaction notes

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