Benzyl Bromide → HCID 21764986, compound

HRID 434320Notes

Reaction equation

HRID 434320 reaction equation
[OH:1][CH2:2][C@H:3]1[C@H:7]([CH2:8][OH:9])[O:6][CH:5]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[O:4]1.[OH-].[K+].[CH2:18](Br)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>>[CH2:18]([O:9][CH2:8][C@H:7]1[C@H:3]([CH2:2][O:1][CH2:5][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[O:4][CH:5]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[O:6]1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

4

Reactant 3

HCID 7498Benzyl BromideHCID 14797Potassium HydroxideHCID 719727(2-Phenyl-1,3-dioxolane-4,5-diyl)dimethanol

Product 1

HCID 21764986HCID 21764986, compound

Conditions

Temperature
80 °C

Procedure

15 g (71.4 mMol) (4S,5S)-4,5-dihydroxymethyl-2-phenyl-1,3-dioxolan are rendered completely anhydrous by evaporating 2× with 300 ml toluene and the oil remaining in the reaction vessel is dissolved in 150 ml toluene, 30 g powdered KOH (535 mMol) and 71.5 g (418 mMol) benzyl bromide are added and the reaction mixture stirred for 15 hours at 80° C. The mixture is cooled, the remaining toluene-phase decanted, and the inorganic component removed from the residual phase by stirring 2× with 200 ml toluene and decanting. The combined toluene phases are filtered through talc, evaporated and the remaining oil filtered fraction-wise through 2 kg silica gel 60 using methylene chloride as solvent. Fractions containing benzyl bromide are disposed of. The title compound is obtained as a light yellow fluid with a rotation of [α]D20 =+10.1 (±1)° (c=1.4 in chloroform).

Workup

  1. customby evaporating 2× with 300 ml toluene
  2. dissolutionis dissolved in 150 ml toluene
  3. temperatureThe mixture is cooled
  4. customthe remaining toluene-phase decanted
  5. customthe inorganic component removed from the residual phase
  6. stirringby stirring 2× with 200 ml toluene
  7. customdecanting
  8. filtrationThe combined toluene phases are filtered through talc
  9. customevaporated
  10. filtrationthe remaining oil filtered fraction-wise through 2 kg silica gel 60 using methylene chloride as solvent
  11. additionFractions containing benzyl bromide

Sources & evidence

ORD record
ord-9054bcd57e464f04bfaf465d8e025684
Source dataset
uspto-grants-1983_08
Patent number
US04396542

Reaction notes

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