Benzyl Chloride → HCID 13309735, compound

HRID 1903887Notes

Reaction equation

HRID 1903887 reaction equation
[CH3:1][C:2]1([CH2:9][OH:10])[CH2:7][CH2:6][CH:5]=[C:4]([CH3:8])[O:3]1.[CH2:11](Cl)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>[OH-].[Na+].C(Cl)Cl.S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.O>[CH3:1][C:2]1([CH2:9][O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:7][CH2:6][CH:5]=[C:4]([CH3:8])[O:3]1

Participants

7

Reactant 2

HCID 7503Benzyl ChlorideHCID 12867349HCID 12867349, compound

Product 1

HCID 13309735HCID 13309735, compoundYield 80.2%

Reagents, catalysts & solvents 4

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent2×HCID 14798Sodium HydroxideSolvent

Procedure

A mixture of 3,4-dihydro-2,6-dimethyl-2H-pyran-2-methanol (5.8 g) and benzyl chloride (5.2 g) in 50% aqueous sodium hydroxide (16 g) and 10 ml methylene chloride was treated with 0.7 g tetrabutylammonium hydrogen sulfate. After stirring vigorously for 21 hours at room temperature, the mixture was diluted with more methylene chloride and water to facilitate phase separation. The organic phase was separated, washed with water, dried over potassium carbonate and concentrated. Distillation gave 7.6 g colorless liquid with bp 101°-102° C. (0.02 torr).

Workup

  1. customphase separation
  2. customThe organic phase was separated
  3. washwashed with water
  4. dry with materialdried over potassium carbonate
  5. concentrationconcentrated
  6. distillationDistillation

Sources & evidence

ORD record
ord-730becfb76774087b27374fee9c5abf5
Source dataset
uspto-grants-1984_03
Patent number
US04439225

Reaction notes

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