Propylene Glycol → 2,4-Dimethyl-2-(3-methyl-2-chloroacetamidophenyl) dioxolane

HRID 358175Notes

Reaction equation

HRID 358175 reaction equation
[Cl:1][CH2:2][C:3]([NH:5][C:6]1[C:11]([C:12](=[O:14])[CH3:13])=[CH:10][CH:9]=[CH:8][C:7]=1[CH3:15])=[O:4].[CH2:16](O)[CH:17]([OH:19])[CH3:18].C1(C)C(S(O)(=O)=O)=CC=CC=1>C1(C)C=CC=CC=1>[CH3:13][C:12]1([C:11]2[CH:10]=[CH:9][CH:8]=[C:7]([CH3:15])[C:6]=2[NH:5][C:3](=[O:4])[CH2:2][Cl:1])[O:19][CH:17]([CH3:18])[CH2:16][O:14]1

Participants

5

Reactant 3

HCID 1030Propylene GlycolHCID 69252-Methylbenzenesulfonic acidHCID 15581074HCID 15581074, compound

Product 1

HCID 133621302,4-Dimethyl-2-(3-methyl-2-chloroacetamidophenyl) dioxolane

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

N-chloroacetyl-2-methyl-6-acetylaniline (from Example 1), 4.51 g, 1,2-propanediol, 3.7 ml, and a dash of toluene sulfonic acid were combined in 50 ml toluene and refluxed. The distilled water by-product was collected in a Dean-Stark trap. After water ceased to distil, methylene chloride was added and the mixture was extracted successively with bicarbonate solution and water, then dried (MgSO4) and evaporated to yield 3.3 g brown oil. The oil was purified on a silica gel column (Hexane:ethyl acetate eluant) to yield the title product (Compound No. 2 in Table A).

Workup

  1. temperaturerefluxed
  2. distillationThe distilled water by-product was collected in a Dean-Stark trap
  3. customto distil
  4. additionmethylene chloride was added
  5. extractionthe mixture was extracted successively with bicarbonate solution and water
  6. dry with materialdried (MgSO4)
  7. customevaporated

Sources & evidence

ORD record
ord-2a1acdf25a764fdc8089f1976432e222
Source dataset
uspto-grants-1984_08
Patent number
US04465502

Reaction notes

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