Ethyl bromoacetate → 2-[4-(Hexafluoro-2-hydroxy-2-propyl)-2-methoxy-6-methylphenoxy]acetic acid

HRID 1680252Notes

Reaction equation

HRID 1680252 reaction equation
[F:1][C:2]([F:20])([F:19])[C:3]([C:9]1[CH:14]=[C:13]([CH3:15])[C:12]([OH:16])=[C:11]([O:17][CH3:18])[CH:10]=1)([OH:8])[C:4]([F:7])([F:6])[F:5].Br[CH2:22][C:23]([O:25]CC)=[O:24].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[F:1][C:2]([F:19])([F:20])[C:3]([C:9]1[CH:14]=[C:13]([CH3:15])[C:12]([O:16][CH2:22][C:23]([OH:25])=[O:24])=[C:11]([O:17][CH3:18])[CH:10]=1)([OH:8])[C:4]([F:6])([F:5])[F:7]

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 12898563HCID 12898563, compound

Product 1

HCID 128985552-[4-(Hexafluoro-2-hydroxy-2-propyl)-2-methoxy-6-methylphenoxy]acetic acid

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To the above phenol (6.0 g=20 mmol) in 100 ml acetonitrile add ethyl bromoacetate (3.0 g=24 mmol) and potassium carbonate (5.4 g=39 mmol). Stir 16 hours, filter, concentrate, and partition between ether and 1.0 N HCl. Dry and concentrate the ether. Partition between 1:1 ether-hexane and 1.0 N NaOH. Acidify the aqueous layer with concentrated HCl and extract with ether. Dry and concentrate. Recrystallize from ether-hexane and dry at 0.1 mm pressure to obtain 2-[4-(hexafluoro-2-hydroxy-2-propyl)-2-methoxy-6-methylphenoxy]acetic acid, m.p. 111°-113° C.

Workup

  1. filtrationfilter
  2. concentrationconcentrate
  3. custompartition between ether and 1.0 N HCl
  4. customDry
  5. concentrationconcentrate the ether
  6. customPartition between 1:1 ether-hexane and 1.0 N NaOH
  7. extractionextract with ether
  8. customDry
  9. concentrationconcentrate
  10. customRecrystallize from ether-hexane
  11. customdry at 0.1 mm pressure

Sources & evidence

ORD record
ord-29369664fbdd4f8eb2d22c45d5a7f382
Source dataset
uspto-grants-1981_06
Patent number
US04272550

Reaction notes

Loading…