Benzyl Chloride → HCID 20364965, compound

HRID 1679009Notes

Reaction equation

HRID 1679009 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH:6]1[O:11][CH2:10][CH:9]([OH:12])[CH2:8][O:7]1.[H-].[Na+].[H][H].[CH2:17](Cl)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>C1(C)C=CC=CC=1>[CH2:17]([O:12][CH:9]1[CH2:10][O:11][CH:6]([C:2]2[O:1][CH:5]=[CH:4][CH:3]=2)[O:7][CH2:8]1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

6

Reactant 4

HCID 7503Benzyl ChlorideHCID 24758Sodium hydrideHCID 296874m-Dioxan-5-ol, 2-(2-furyl)-HCID 178418361HCID 178418361, compound

Product 1

HCID 20364965HCID 20364965, compoundYield 86.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
70 °C

Procedure

To a stirred solution of 17 g of 2-(2-furyl)-5-hydroxy-1,3-dioxane in 150 ml of toluene was added over a period of twenty minutes 4.4 g of sodium hydride (54.7% in mineral oil). The mixture was allowed to stir for 1 hour to permit evolution of by-product hydrogen, after which time 12.7 g of benzyl chloride was added during 15 minutes. The reaction mixture was heated to 70° C and maintained thereat for ca. 21 hours. The reaction mixture was allowed to cool to room temperature and remain at that temperature for 4 days. The mixture was washed with two 250-ml volumes of water, which aqueous washes were combined and extracted with toluene (three 150-ml volumes) to recover product. The toluene solution was combined with the washed reaction mixture and the total mixture was dried over magnesium sulfate, filtered and evaporated under reduced pressure to give 22.5 g of amber oil. The oil was washed with 25 ml of hexane, which procedure produced 17.5 g of clear oil. The clear oil was distilled and those fractions boiling at a bath temperature of 144°-154° C under 2 × 10-4 mm Hg (bath temp. 144°-147°; nD25 1.5349: bath temp. 148°-154°; nD25 1.5379) were combined (10.6 g) and a portion was submitted for elemental analysis. Upon refrigeration for ca. 48 hours, 0.5 g of crystalline 5-benzyloxy-2-(2-furyl)-1,3-dioxane precipitated, m.p. 58.5°-61° C.

Workup

  1. temperaturemaintained
  2. waitfor ca. 21 hours
  3. temperatureto cool to room temperature
  4. waitremain at that temperature for 4 days
  5. washThe mixture was washed with two 250-ml volumes of water, which aqueous washes
  6. extractionextracted with toluene (three 150-ml volumes)
  7. customto recover product
  8. customThe toluene solution was combined with the washed reaction mixture
  9. dry with materialthe total mixture was dried over magnesium sulfate
  10. filtrationfiltered
  11. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-8eb0b5d1cd3943ef803c166fb8c33666
Source dataset
uspto-grants-1978_03
Patent number
US04077982

Reaction notes

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