Epichlorohydrin → HCID 54348861, compound

HRID 1938123Notes

Reaction equation

HRID 1938123 reaction equation
C[C:2]([CH3:5])([O-:4])[CH3:3].[K+].[OH:7][C:8]1[CH:27]=[CH:26][C:11]([C:12]([O:14][CH2:15][O:16][C:17](=[O:25])[C:18]2[CH:23]=[CH:22][C:21]([OH:24])=[CH:20][CH:19]=2)=[O:13])=[CH:10][CH:9]=1.[CH2:28]([CH:30]1[O:32][CH2:31]1)Cl>CN(C=O)C>[O:32]1[CH2:31][CH:30]1[CH2:28][O:7][C:8]1[CH:9]=[CH:10][C:11]([C:12]([O:14][CH2:15][O:16][C:17](=[O:25])[C:18]2[CH:23]=[CH:22][C:21]([O:24][CH2:3][CH:2]3[O:4][CH2:5]3)=[CH:20][CH:19]=2)=[O:13])=[CH:26][CH:27]=1

Participants

5

Reactant 3

HCID 7835EpichlorohydrinHCID 23665647Potassium tert-butoxideHCID 59444500HCID 59444500, compound

Product 1

HCID 54348861HCID 54348861, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Potassium tert.butoxide (1.347 g, 12.00 mmol) is added to a solution of methylene di(p-hydroxybenzoate) prepared as described in Example 4(o) (1,728 g, 6.00 mmol) in DMF (75 ml), under a dry N2 atmosphere. Epichlorohydrin (2.22 g, 24.00 mmol) is added and after 24 hours at 20° C. the solvent is removed under reduced pressure. The residue is dissolved by adding dichloromethane (75 ml) and water (30 ml) and adjusting the pH to neutral using hydrochloric acid (1 M). After separating the phases the dichloromethane layer is washed with water (3×30 ml). The organic phase is dried (MgSO4) and the solvent removed under reduced pressure to give 1.22 g (51%) product as a colourless oil. 1H NMR (60 MHz, CDCl3): δ2.8 (4H, m, 2×epoxy--CH2), 3.3 (2H, m, 2×epoxy--CH), 4.05 (2H, dd, J=22, 11 Hz, 2×O--CH--H), 4.12 (2H, dd, J=22, 11 Hz, 2×O--CH--H), 6.14 (2H, s, O--CH2 --O), 6.9 (4H, m, 2×Ar), 7.9 (4H, m, 2×Ar).

Workup

  1. customprepared
  2. customis removed under reduced pressure
  3. dissolutionThe residue is dissolved
  4. additionby adding dichloromethane (75 ml) and water (30 ml)
  5. customAfter separating the phases the dichloromethane layer
  6. washis washed with water (3×30 ml)
  7. dry with materialThe organic phase is dried (MgSO4)
  8. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-133a488721ce41268d15b21cae4a9f49
Source dataset
uspto-grants-1997_12
Patent number
US05693321

Reaction notes

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