Epichlorohydrin → 4-Benzyloxy-7-(2,3-epoxypropyloxy)coumarin

HRID 444214Notes

Reaction equation

HRID 444214 reaction equation
[CH2:1]([O:8][C:9]1[C:18]2[C:13](=[CH:14][C:15]([OH:19])=[CH:16][CH:17]=2)[O:12][C:11](=[O:20])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[K+].[CH2:23]([CH:25]1[O:27][CH2:26]1)Cl>C(O)C.O>[CH2:1]([O:8][C:9]1[C:18]2[C:13](=[CH:14][C:15]([O:19][CH2:23][CH:25]3[O:27][CH2:26]3)=[CH:16][CH:17]=2)[O:12][C:11](=[O:20])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 7835EpichlorohydrinHCID 14797Potassium HydroxideHCID 134084074-Benzyloxy-7-hydroxycoumarin

Product 1

HCID 134084084-Benzyloxy-7-(2,3-epoxypropyloxy)coumarin

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

4-Benzyloxy-7-hydroxycoumarin (10.7 g, 0.041 mole) was dissolved in ethanol (200 ml) and a solution of potassium hydroxide (2.5 g) in water (10 ml) was added. Epichlorhydrin (40 ml) was added and the stirred mixture heated to reflux for 21/2 hr. After cooling, the solvent was removed in vacuo and the residue partitioned between water and ethyl acetate. Evaporation of the dried (MgSO4) organic phase gave the product as a white crystalline solid. Recrystallization from ethanol gave 11.1 g (83%) of material of m.p. 128°-129° C.; (Found; C, 70.48; H, 4.92; C19H16O5 requires; C, 70.36; H, 4.97%).

Workup

  1. temperaturethe stirred mixture heated
  2. temperatureto reflux for 21/2 hr
  3. temperatureAfter cooling
  4. customthe solvent was removed in vacuo
  5. customthe residue partitioned between water and ethyl acetate
  6. customEvaporation of the
  7. dry with materialdried (MgSO4) organic phase

Sources & evidence

ORD record
ord-9d0ac0a5027940a7aa31852e5a9d8c75
Source dataset
uspto-grants-1981_04
Patent number
US04263299

Reaction notes

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