Water → HCID 54568868, compound

HRID 259295Notes

Reaction equation

HRID 259295 reaction equation
[C:1]([O-:4])(=[O:3])[CH3:2].[Na+].C(OCC)C.O.Br[CH2:13][C:14]([CH3:28])=[CH:15][C:16]([O:18][CH2:19][CH2:20][O:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:17]>>[C:1]([O:4][CH2:13][C:14]([CH3:28])=[CH:15][C:16]([O:18][CH2:19][CH2:20][O:21][C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)=[O:17])(=[O:3])[CH3:2]

Participants

5

Reactant 4

HCID 962WaterHCID 3283Diethyl EtherHCID 517045Sodium AcetateHCID 544220992-Phenoxyethyl 4-bromo-3-methylbut-2-enoate2×

Product 1

HCID 54568868HCID 54568868, compound

Procedure

β-phenoxyethyl 4-bromo-3-methyl-2-butenoate (15g) obtained in Example 7 was refluxed with anhydrous sodium acetate (5.32g) in glacial acetic acid (15g) for 8 hours. Ethylether (300ml) and water (20ml) were added to the reaction mixture and the ether layer was washed with water, dried, and concentrated, giving a crude product (11.7g). The crude product on fractionation gave a fractionation gave a fraction (6.1g), b.p. 165°-168° C./0.6mmHg. Structural assignment for this compound was made from its infrared absorption spectrum; 1738, 1710, 1658, 1600, 1590, 1500, 1240, 1215, 1145, 1055, 1040, 755, and 690cm-1.

Workup

  1. washthe ether layer was washed with water
  2. customdried
  3. concentrationconcentrated
  4. customgiving a crude product (11.7g)

Sources & evidence

ORD record
ord-83a6475c4487416fa4bab396754f0584
Source dataset
uspto-grants-1977_07
Patent number
US04036984

Reaction notes

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