Ethyl bromoacetate → Acetic acid, [[5′-(acetyloxy)[1,1′:3′,1′′-terphenyl]-2′-yl]oxy]-, ethyl ester

HRID 1160423Notes

Reaction equation

HRID 1160423 reaction equation
[C:1]([O:4][C:5]1[CH:10]=[C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:8]([OH:17])=[C:7]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:6]=1)(=[O:3])[CH3:2].Br[CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27].C(=O)([O-])[O-].[K+].[K+]>CC(=O)CC>[C:1]([O:4][C:5]1[CH:6]=[C:7]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:8]([O:17][CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27])=[C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:10]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 12544153HCID 12544153, compound

Product 1

HCID 21907769Acetic acid, [[5′-(acetyloxy)[1,1′:3′,1′′-terphenyl]-2′-yl]oxy]-, ethyl esterYield 92.2%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A mixture of 4-acetoxy-2,6-diphenylphenol (6.1 g, 20 mmol; prepared as described in Ber. 101, 2519 (1968) ), ethyl bromoacetate (4.0 g, 24 mmol), potassium carbonate (3.3 g, 24 mmol) and 2-butanone (150 ml) was refluxed for 24 h, then filtered and the solvent evaporated. The residue was purified by chromatography on silica gel (120 g, eluent benzene) to give 7.2 g (92%) of oily ethyl 4-acetoxy-2,6-diphenylphenoxyacetate .

Workup

  1. temperaturewas refluxed for 24 h
  2. filtrationfiltered
  3. customthe solvent evaporated
  4. customThe residue was purified by chromatography on silica gel (120 g, eluent benzene)

Sources & evidence

ORD record
ord-813a606f0b2a4d299bd979462c688255
Source dataset
uspto-grants-2010_10
Patent number
US07816385B2

Reaction notes

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