Potassium Carbonate → 2-(4-(3,5-Bis(hydroxymethyl)phenoxy)butyl)isoindoline-1,3-dione

HRID 1051845Notes

Reaction equation

HRID 1051845 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH2:10][OH:11])[CH:5]=[C:6]([CH2:8][OH:9])[CH:7]=1.Br[CH2:13][CH2:14][CH2:15][CH2:16][N:17]1[C:25](=[O:26])[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[C:18]1=[O:27].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[OH:9][CH2:8][C:6]1[CH:7]=[C:2]([CH:3]=[C:4]([CH2:10][OH:11])[CH:5]=1)[O:1][CH2:13][CH2:14][CH2:15][CH2:16][N:17]1[C:25](=[O:26])[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[C:18]1=[O:27]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 93575N-(4-Bromobutyl)phthalimideHCID 15194153,5-Di(hydroxymethyl)phenol

Product 1

HCID 860192882-(4-(3,5-Bis(hydroxymethyl)phenoxy)butyl)isoindoline-1,3-dioneYield 78%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a stirred solution of (5-hydroxy-1,3-phenylene)dimethanol (7.27 g, 47 mmol, 1 eq.) in 200 mL of acetonitrile at room temperature, 2-(4-bromobutyl)isoindoline-1,3-dione (1.2 eq.) and potassium carbonate (K2CO3, 2 eq.) were slowly added. The resultant mixture was then heated at reflux for 8 hours, after which the volatiles were removed, and the residue was partitioned between EtOAc and water. The EtOAc layer was washed with brine and dried over MgSO4. Evaporation of EtOAc gave 2-(4-(3,5-bis(hydroxymethyl)phenoxy)butyl)isoindoline-1,3-dione (13 g, 78% yield).

Workup

  1. temperatureat reflux for 8 hours
  2. customafter which the volatiles were removed
  3. customthe residue was partitioned between EtOAc and water
  4. washThe EtOAc layer was washed with brine
  5. dry with materialdried over MgSO4
  6. customEvaporation of EtOAc

Sources & evidence

ORD record
ord-485553b693eb47b0b186cba689c5fbd3
Source dataset
uspto-grants-2016_07
Patent number
US09388193B2

Reaction notes

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