Toluene → HCID 69933131, compound

HRID 585337Notes

Reaction equation

HRID 585337 reaction equation
[OH:1][CH2:2][C:3]1[CH:8]=[C:7]([CH2:9][OH:10])[CH:6]=[CH:5][C:4]=1[Br:11].OCC1C=CC=[C:16]([CH2:20][OH:21])C=1Br.[CH:23]([O:25][CH2:26][CH3:27])=[CH2:24].C(=O)([O-])[O-].[Na+].[Na+].[C:34]1(C)C=CC=C[CH:35]=1>O.C1(C)C=CC(S(O)(=O)=O)=CC=1>[CH2:23]([O:25][CH2:26][CH2:27][O:1][CH2:2][C:3]1[CH:8]=[C:7]([CH2:9][O:10][CH2:34][CH2:35][O:21][CH2:20][CH3:16])[CH:6]=[CH:5][C:4]=1[Br:11])[CH3:24]

Participants

7

Reactant 5

HCID 1140TolueneHCID 8023Ethyl vinyl etherHCID 10340Sodium CarbonateHCID 12968884[2-Bromo-5-(hydroxymethyl)phenyl]methanolHCID 15468755(2-Bromo-1,3-phenylene)dimethanol

Product 1

HCID 69933131HCID 69933131, compoundYield 97.1%

Reagents, catalysts & solvents 1

HCID 521998p-Toluenesulfonic acid monohydrateCatalyst

Procedure

To a suspension obtained by dispersing an about 93:7 mixture (22.1 g) of 2,4-bis(hydroxymethyl)bromobenzene and 2,6-bis(hydroxymethyl)bromobenzene, and p-toluenesulfonic acid monohydrate (0.1 g) in toluene (220 ml) was added dropwise ethyl vinyl ether (18.4 g) at 24-32° C., and the mixture was stirred at room temperature for 2 hr. The reaction mixture was poured into 5% aqueous sodium carbonate solution (100 ml), and the organic layer was washed with 5% aqueous sodium carbonate solution (100 ml), and dried over potassium carbonate. The solvent was evaporated to give an about 93:7 mixture (35.7 g, 97.1%) of 2,4-bis(1′-ethoxyethoxymethyl)bromobenzene and 2,6-bis(1′-ethoxyethoxymethyl)bromobenzene as a yellow oil. 2,4-bis(1′-Ethoxyethoxymethyl)bromobenzene was isolated by preparative HPLC and used in the measurement.

Workup

  1. customTo a suspension obtained
  2. washthe organic layer was washed with 5% aqueous sodium carbonate solution (100 ml)
  3. dry with materialdried over potassium carbonate
  4. customThe solvent was evaporated

Sources & evidence

ORD record
ord-5dfc70a4a08f4c4fa20d9bbd201dca06
Source dataset
uspto-grants-2005_08
Patent number
US06930211B2

Reaction notes

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