Boric Acid → 2,3-Dihydroxypropyl 4-dimethylaminobenzoate

HRID 251520Notes

Reaction equation

HRID 251520 reaction equation
[CH3:1][N:2]([CH3:20])[C:3]1[CH:8]=[CH:7][C:6]([C:9]([O:11][CH2:12][CH:13]2[CH2:17][O:16]C(C)(C)[O:14]2)=[O:10])=[CH:5][CH:4]=1.B(O)(O)O>COCCOCCOC.O>[CH3:1][N:2]([CH3:20])[C:3]1[CH:4]=[CH:5][C:6]([C:9]([O:11][CH2:12][CH:13]([OH:14])[CH2:17][OH:16])=[O:10])=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 7628Boric AcidHCID 580901264-(4-Dimethylaminophenylcarbonyloxymethyl)-2,2-dimethyl-1,3-dioxolane

Product 1

HCID 580901212,3-Dihydroxypropyl 4-dimethylaminobenzoate

Reagents, catalysts & solvents 1

HCID 86618275Diglyme waterSolvent

Conditions

Temperature
100 °C

Procedure

4-(4-Dimethylaminophenylcarbonyloxymethyl)-2,2-dimethyl-1,3-dioxolane from Example 4 (3 mmol) is dissolved in the diglyme/H2O 8:2 mixture (25 ml), and boric acid (2 g) is added. The reaction mixture is stirred at 100° C. for 3 h. The solvent is then distilled off in vacuo, the crude product which remains is taken up in water (100 ml) and extracted with ethyl acetate (3×20 ml). The combined organic phases are washed with water (2×50 ml) and dried over magnesium sulfate. The crude product remaining after evaporation of the ethyl acetate in vacuo is employed without further purification for subsequent reactions.

Workup

  1. additionis added
  2. distillationThe solvent is then distilled off in vacuo
  3. extractionextracted with ethyl acetate (3×20 ml)
  4. washThe combined organic phases are washed with water (2×50 ml)
  5. dry with materialdried over magnesium sulfate
  6. customafter evaporation of the ethyl acetate in vacuo
  7. customis employed without further purification for subsequent reactions

Sources & evidence

ORD record
ord-1521a1c10ee943cc8a78ca3b2ba49c83
Source dataset
uspto-grants-2011_01
Patent number
US07863478B2

Reaction notes

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