Water → (2R)-1-(benzyloxy)propan-2-ol

HRID 1493092Notes

Reaction equation

HRID 1493092 reaction equation
O1CCCCC1[O:7][C@H:8]([CH3:11])[CH2:9][OH:10].[H-].[Na+].[CH2:14](Br)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.O>C1COCC1.CN(C=O)C>[CH2:14]([O:10][CH2:9][C@H:8]([OH:7])[CH3:11])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

7

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 9793900(2R)-2-((tetrahydro-2H-pyran-2-yl)oxy)propan-1-ol

Product 1

HCID 10953891(2R)-1-(benzyloxy)propan-2-olYield 45.5%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

(2R)-2-tetrahydropyranyloxy-1-hydroxypropane (60 g, 0.37 mol) was dropwise added to a suspension of sodium hydride (60%) (22 g) in THF (100 ml) under ice cooling. After completion of the dropwise addition, a solution of benzyl bromide (70 g) in DMF (300 ml) was dropwise added, followed by agitating the mixture at room temperature for 6 hours, pouring it into water (500 ml), extracting with toluene (300 ml), washing the resulting organic layer with water, concentrating it, dissolving the concentrate in ethanol (300 ml), adding 6N-hydrochloric acid (20 ml), agitating the mixture at 20° C. for 2 hours, distilling off ethanol, adding toluene (300 ml), washing the resulting organic layer with an alkali and then with water and distilling it under reduced pressure to obtain (R)-1-benzyloxy-2-propanol (b.p. 105°-107° C./5 mmHg) (28 g).

Workup

  1. additionAfter completion of the dropwise addition
  2. extractionextracting with toluene (300 ml)
  3. washwashing the resulting organic layer with water
  4. concentrationconcentrating it
  5. dissolutiondissolving the
  6. concentrationconcentrate in ethanol (300 ml)
  7. additionadding 6N-hydrochloric acid (20 ml)
  8. stirringagitating the mixture at 20° C. for 2 hours
  9. distillationdistilling off ethanol
  10. additionadding toluene (300 ml)
  11. washwashing the resulting organic layer with an alkali and then with water
  12. distillationdistilling it under reduced pressure

Sources & evidence

ORD record
ord-3bd22518c69e4fb1838e971ccc1b9953
Source dataset
uspto-grants-1991_06
Patent number
US05021191

Reaction notes

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