Epichlorohydrin → HCID 54348861, compound

HRID 580798Notes

Reaction equation

HRID 580798 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) (1.728 g, 6.00 mmol) prepared as described in Example 15 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 (1M). 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): δ 2.8 (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-eb6de4ae06a14e66adf89e635612502f
Source dataset
uspto-grants-1999_07
Patent number
US05919753

Reaction notes

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