Methyl Ethyl Ketone → HCID 20309476, compound

HRID 1763308Notes

Reaction equation

HRID 1763308 reaction equation
[Cl:1][C:2]1[CH:16]=[CH:15][C:5]([C:6]([CH2:8][CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])=[O:7])=[C:4]([OH:17])[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].C[C:25](=[O:28])[CH2:26][CH3:27]>>[Cl:1][C:2]1[CH:16]=[CH:15][C:5]([C:6]([CH2:8][CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])=[O:7])=[C:4]([O:17][CH2:27][CH:26]2[O:28][CH2:25]2)[CH:3]=1

Participants

4

Reactant 3

HCID 6569Methyl Ethyl KetoneHCID 11430Potassium CarbonateHCID 20309489HCID 20309489, compound

Product 1

HCID 20309476HCID 20309476, compoundYield 86%

Procedure

A well stirred mixture of ethyl 3-(4-chloro-2-hydroxybenzoyl)propionate (9.6 g, 0.037 mole), potassium carbonate (5.96 g, 0.043 mole) epibromohydrin (14.4 ml, 0.173 mole) and dry butan-2-one (250 ml) was heated under reflux for 28 hours. Evaporation of the filtered solution under reduced pressure and purification of the residue by column chromatography gave ethyl 3-[4-chloro-2-(2,3-epoxypropoxy)benzoyl]-propionate as an oil (10.0 g, 86%). (Found: M+, 312/314. C15H17ClO5. requires M, 312/314).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 28 hours
  3. customEvaporation of the filtered solution
  4. customunder reduced pressure and purification of the residue by column chromatography

Sources & evidence

ORD record
ord-e1bcec5f0f114d49a080f50e89f20458
Source dataset
uspto-grants-1978_09
Patent number
US04111936

Reaction notes

Loading…