Chloromethyl Methyl Ether → HCID 13488867, compound

HRID 1589696Notes

Reaction equation

HRID 1589696 reaction equation
[OH:1][C:2]1[C:3]([CH3:17])=[C:4]2[C:9](=[C:10]([CH3:13])[C:11]=1[CH3:12])[O:8][C:7]([CH2:15][OH:16])([CH3:14])[CH2:6][CH2:5]2.[H-].[Na+].[CH3:20][O:21][CH2:22]Cl>CN(C)C=O.C1C=CC=CC=1>[CH3:20][O:21][CH2:22][O:1][C:2]1[C:3]([CH3:17])=[C:4]2[C:9](=[C:10]([CH3:13])[C:11]=1[CH3:12])[O:8][C:7]([CH2:15][OH:16])([CH3:14])[CH2:6][CH2:5]2

Participants

6

Reactant 3

HCID 7864Chloromethyl Methyl EtherHCID 24758Sodium hydrideHCID 117466322-Hydroxymethyl-2,5,7,8-tetramethyl-chroman-6-ol

Product 1

HCID 13488867HCID 13488867, compound

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 6228DimethylformamideSolvent

Procedure

16.1 g of 6-hydroxy-2,5,7,8-tetramethylchroman-2-ylmethanol were dissolved in 70 ml of dry dimethylformamide. 3.0 g of a 50% w/w suspension of sodium hydride in oil (which had been washed with cyclohexane 3 times) were added gradually to the resulting solution at 5°-10° C., with stirring and under a nitrogen stream. The mixture was reacted for 1 hour at room temperature, and then the solution was ice-cooled to 3°-5° C., and 5.5 g of chloromethyl methyl ether dissolved in 40 ml of dry benzene were added dropwise. After the whole of this had been added, the solution was reacted for 1 hour at room temperature. The reaction mixture was then poured into ice-water and extracted with cyclohexane. The extract was washed four times with a 5% w/v aqueous solution of sodium hydroxide, and then with water. It was then dried and the solvent was distilled off under reduced pressure, giving the desired 6-(methoxymethoxy)-2,5,7,8-tetramethylchroman-2-ylmethanol. On thin layer chromatography, the Rf value was 0.45 [silica gel; developing solvent:benzene:ethyl acetate=4:1 by volume].

Workup

  1. washin oil (which had been washed with cyclohexane 3 times)
  2. additionwere added gradually to the resulting solution at 5°-10° C.
  3. customThe mixture was reacted for 1 hour at room temperature
  4. temperaturecooled to 3°-5° C.
  5. additionwere added dropwise
  6. additionAfter the whole of this had been added
  7. customthe solution was reacted for 1 hour at room temperature
  8. extractionextracted with cyclohexane
  9. washThe extract was washed four times with a 5% w/v aqueous solution of sodium hydroxide
  10. customIt was then dried
  11. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-4c500d0692774af79bdee1cba77c7aa5
Source dataset
uspto-grants-1986_02
Patent number
US04572912

Reaction notes

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