Water → HCID 54467674, compound

HRID 2083404Notes

Reaction equation

HRID 2083404 reaction equation
[CH3:1][N:2]([CH3:19])[C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[O:14][CH2:13][C:12]([CH3:18])([CH:15]([CH3:17])[OH:16])[CH2:11][O:10]2)=[CH:5][CH:4]=1.N1C=CC=CC=1.[C:26](Cl)(=[O:28])[CH3:27].O>C1C=CC=CC=1>[C:26]([O:16][CH:15]([CH3:17])[C:12]1([CH3:18])[CH2:11][O:10][CH:9]([C:6]2[CH:5]=[CH:4][C:3]([N:2]([CH3:19])[CH3:1])=[CH:8][CH:7]=2)[O:14][CH2:13]1)(=[O:28])[CH3:27]

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 6367Acetyl chlorideHCID 20358502HCID 20358502, compound

Product 1

HCID 54467674HCID 54467674, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

2-[4-(Dimethylamino)phenyl]-α,5-dimethyl-1,3-dioxan-5-methanol (195 mg), dry pyridine (2.0 ml), and acetyl chloride (1.0 ml), in benzene (10 ml) were refluxed for 3 hrs. The cooled mixture was poured into water and extracted with ethyl acetate. The combined extracts were washed with water, dried (MgSO4), and evaporated. The residue was purified by preparative layer chromatography on silica gel (eluting with benzeneethyl acetate 5:1) and distilled to give an oil, b.p. 155°-160°/0.05 torr.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe combined extracts were washed with water
  3. dry with materialdried (MgSO4)
  4. customevaporated
  5. customThe residue was purified by preparative layer chromatography on silica gel (eluting with benzeneethyl acetate 5:1)
  6. distillationdistilled
  7. customto give an oil, b.p. 155°-160°/0.05 torr

Sources & evidence

ORD record
ord-25b771fa5e9841d5862cf15f283ec872
Source dataset
uspto-grants-1978_04
Patent number
US04085222

Reaction notes

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