Benzyl Chloride → HCID 20364866, compound

HRID 1679000Notes

Reaction equation

HRID 1679000 reaction equation
[H-].[Na+].[OH:3][CH:4]1[CH2:9][O:8][CH:7]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([F:16])[CH:11]=2)[O:6][CH2:5]1.[CH2:17](Cl)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>C1C=CC=CC=1.C1(C)C(C)=CC=CC=1>[CH2:17]([O:3][CH:4]1[CH2:9][O:8][CH:7]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([F:16])[CH:11]=2)[O:6][CH2:5]1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

6

Reactant 3

HCID 7503Benzyl ChlorideHCID 24758Sodium hydrideHCID 20364909HCID 20364909, compound

Product 1

HCID 20364866HCID 20364866, compoundYield 71.2%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 7237O-XyleneSolvent

Procedure

A slurry of sodium hydride (3.7 g of 62%, 0.096 mole) in benzene (100 ml) and xylene (100 ml) was stirred at ambient temperature while 5-hydroxy-2-(3-fluorophenyl)-1,3-dioxane (18.9 g, 0.096 mole) was added dropwise during 1 hour. This mixture was stirred 1 additional hour, then to it was added benzyl chloride (12.2 g, 0.096 mole) during 1/2 hour. The mixture was heated under reflux for 18 hours, cooled, filtered and the filtrate washed with water (2 × 200 ml). The washed solution was dried over magnesium sulfate and concentrated to give 19.7 g of oil which was distilled under 2 × 10-4 mm pressure to give three fractions distilling at bath temperature of 98°-119° C (cut 1); 119°-139° C (cut 2); and 139°-143° C (cut 3). Cut 2 (9.1 g) was found by nmr analysis to be a mixture of cis and trans-dioxanes and the corresponding dioxolane. Cut 3 (1.5 g, m.p. 70°-71° C) was found by nmr to be 100% cis-5-benzyloxy-2-(3-fluorophenyl)-1,3-dioxane and this cut was used in further studies.

Workup

  1. additionwas added dropwise during 1 hour
  2. temperatureThe mixture was heated
  3. temperatureunder reflux for 18 hours
  4. temperaturecooled
  5. filtrationfiltered
  6. washthe filtrate washed with water (2 × 200 ml)
  7. dry with materialThe washed solution was dried over magnesium sulfate
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-0516d71a264f43c08cf1027f65080788
Source dataset
uspto-grants-1978_03
Patent number
US04077982

Reaction notes

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