Glycerol → HCID 19742978, compound

HRID 2254649Notes

Reaction equation

HRID 2254649 reaction equation
[CH2:1]([OH:6])[CH:2]([OH:5])[CH2:3][OH:4].[Br:7][CH2:8][C:9]([C:11]1[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=1)=O.CC1C=CC(S(O)(=O)=O)=CC=1.[OH-].[Na+]>O.C1C=CC=CC=1.C(O)CCC>[Br:7][CH2:8][C:9]1([C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=2)[O:5][CH:2]([CH2:3][OH:4])[CH2:1][O:6]1

Participants

8

Reactant 4

HCID 753GlycerolHCID 4965Bromomethyl 4-methoxyphenyl ketoneHCID 6101p-Toluenesulfonic acidHCID 14798Sodium Hydroxide

Product 1

HCID 19742978HCID 19742978, compound

Reagents, catalysts & solvents 3

HCID 241BenzeneSolventHCID 2631-ButanolSolventHCID 962WaterSolvent

Procedure

A mixture of 69 parts of 1,2,3-propanetriol, 142 parts of 2-bromo-1-(4-methoxyphenyl)-ethanone, 6.3 parts of 4-methylbenzenesulfonic acid, 80 parts of 1-butanol and 450 parts of benzene was stirred and refluxed for 20 hours with water separator. The reaction mixture was cooled and poured into a diluted sodium hydroxide solution. The layers were separated and the aqueous phase was extracted twice with methylbenzene. The combined organic phases were washed with water, dried, filtered and evaporated, yielding 186.5 parts of 2-(bromomethyl)-2-(4-methoxyphenyl)-1,3-dioxolane-4-methanol as a residue (interm. 1).

Workup

  1. temperatureThe reaction mixture was cooled
  2. customThe layers were separated
  3. extractionthe aqueous phase was extracted twice with methylbenzene
  4. washThe combined organic phases were washed with water
  5. customdried
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-0363a99da0f04256bf8ce2f953dcb81e
Source dataset
uspto-grants-1993_08
Patent number
US05236944

Reaction notes

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