2,3-Butanediol → 2,4,5-Trimethyl-2-(3-methyl-2-chloroacetamidophenyl) dioxolane

HRID 1389396Notes

Reaction equation

HRID 1389396 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].[OH:16][CH:17]([CH:19](O)[CH3:20])[CH3:18].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1C=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:16][CH:17]([CH3:18])[CH:19]([CH3:20])[O:14]1

Participants

5

Reactant 3

HCID 2622,3-ButanediolHCID 6101p-Toluenesulfonic acidHCID 15581074HCID 15581074, compound

Product 1

HCID 130449282,4,5-Trimethyl-2-(3-methyl-2-chloroacetamidophenyl) dioxolane

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

The product from Example 1 (10.6 g), 2,3-dihydroxy-butane (8.5 g) and p-toluene sulfonic acid (1.5 g) in 200 ml benzene were refluxed to 2 hours, removing water with a Dean-Stark trap. The solution wash washed with 10% NaOH, dried (MgSO4) and stripped. The product was chromatographed on a silica gel column, eluting with 30% ether-hexane. Yield: 3.8 g of the title product, mp 55°-57° C.

Workup

  1. customremoving water with a Dean-Stark trap
  2. washThe solution wash
  3. washwashed with 10% NaOH
  4. dry with materialdried (MgSO4)
  5. customThe product was chromatographed on a silica gel column
  6. washeluting with 30% ether-hexane

Sources & evidence

ORD record
ord-6a73058dc2284f3e8391af3ca2bfb096
Source dataset
uspto-grants-1981_01
Patent number
US04244730

Reaction notes

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