4-Bromophenacyl bromide → p-Bromophenacyl 6-hydroxycaproate

HRID 328346

Reaction equation

HRID 328346 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]([O-:9])=[O:8].[K+].[Br:11][C:12]1[CH:21]=[CH:20][C:15]([C:16](=[O:19])[CH2:17]Br)=[CH:14][CH:13]=1.C1CC2OCCOCCOC3C(OCCOCCOC2CC1)CCCC3>C(#N)C>[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]([O:9][CH2:17][C:16]([C:15]1[CH:20]=[CH:21][C:12]([Br:11])=[CH:13][CH:14]=1)=[O:19])=[O:8]

Participants

5

Reactant 3

HCID 74544-Bromophenacyl bromideHCID 85955Dicyclohexano-18-crown-6HCID 2371282621810-34-4

Product 1

HCID 13272687p-Bromophenacyl 6-hydroxycaproate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 8.5 g. (50 mmoles) of potassium 6-hydroxycaproate, 13.9 g. (50 mmoles) of p-bromophenacyl bromide, 0.75 g. (2 mmoles) of dicyclohexyl-18 -crown-6 in 500 ml. of acetonitrile is refluxed with stirring for 1 hour and stirred at room temperature overnight. The mixture is filtered and the filtrate evaporated to dryness in vacuo. The residual solid is recrystallized from benzene-hexane mixture affording 14.1 g. of p-bromophenacyl 6-hydroxycarproate, m.p. 79°-81° C.

Workup

  1. additionA mixture of 8.5 g
  2. stirringstirred at room temperature overnight
  3. filtrationThe mixture is filtered
  4. customthe filtrate evaporated to dryness in vacuo
  5. customThe residual solid is recrystallized from benzene-hexane mixture
  6. customaffording 14.1 g

Sources & evidence

ORD record
ord-a734423e92bc44cb9dbd3621076924e4
Source dataset
uspto-grants-1977_04
Patent number
US04017504

Linked notes

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