Water → HCID 22416474, compound

HRID 1720849Notes

Reaction equation

HRID 1720849 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[C:14]([CH3:16])[CH3:15])[C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:4][CH:3]=1.ClC1C=CC=C(C(OO)=[O:25])C=1.[OH-].[Na+].O>ClCCl.II>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2([O:25][C:14]2([CH3:15])[CH3:16])[C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 70297m-Chloroperbenzoic acid2×HCID 22416471HCID 22416471, compound

Product 1

HCID 22416474HCID 22416474, compoundYield 71%

Reagents, catalysts & solvents 2

HCID 807IodineCatalyst2×HCID 6344DichloromethaneSolvent

Procedure

A solution of ethyl 2-(4-chlorophenyl)-3-methylbut-2-enoate (11.4 g, 0.048 mol), prepared in Example 1c, m-chloroperbenzoic acid (15.7 g, 0.050 mol) and iodine (0.1 g) in dichloromethane (400 ml) was stirred for 48 hours at 50°-55° c. During this period, the course of the reaction was monitored by analytical thin layer chromatography and three further portions (2.0 g) of m-chloroperbenzoic acid and two further portions (0.1 g) of iodine were added to the mixture. The precipitate which formed during this time was dissolved by the addition of 2N sodium hydroxide solution (40 ml) and iced water (200 ml). The organic phase was then separated and washed with dilute sodium hydroxide solution (100 ml) and then with water (3×200 ml). The solution was dried (sodium sulphate), evaporated in vacuo, and the crude product purified by flash silica column chromatography, eluting with 1,2-dichloroethane, to give the title compound (8.6 g, 71%) as an oil.

Workup

  1. waitDuring this period
  2. additionwere added to the mixture
  3. customThe precipitate which formed during this time
  4. customThe organic phase was then separated
  5. washwashed with dilute sodium hydroxide solution (100 ml)
  6. dry with materialThe solution was dried (sodium sulphate)
  7. customevaporated in vacuo
  8. customthe crude product purified by flash silica column chromatography
  9. washeluting with 1,2-dichloroethane

Sources & evidence

ORD record
ord-5a748aa5a8ce4785af23cc8d54322bf5
Source dataset
uspto-grants-1996_04
Patent number
US05508251

Reaction notes

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