1-Butanol → HCID 178450851, compound

HRID 706185Notes

Reaction equation

HRID 706185 reaction equation
[CH3:1][O:2][C:3](=[O:26])[CH2:4][N:5]1[C:13](=[O:14])[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([O:15][C:16]3[C:21]([CH3:22])=[CH:20][CH:19]=[CH:18][C:17]=3[CH2:23][CH3:24])[CH:11]=2)[C:6]1=[O:25].[Na].Cl.CCOC(C)=O.[CH2:35](O)[CH2:36][CH2:37]C>>[CH2:1]([O:2][C:3]([C:4]1[N:5]=[C:6]([OH:25])[C:7]2[C:12]([C:13]=1[OH:14])=[CH:11][C:10]([O:15][C:16]1[C:21]([CH3:22])=[CH:20][CH:19]=[CH:18][C:17]=1[CH2:23][CH3:24])=[CH:9][CH:8]=2)=[O:26])[CH2:35][CH2:36][CH3:37]

Participants

6

Reactant 5

HCID 2631-Butanol2×HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 5360545SodiumHCID 67110421HCID 67110421, compound

Product 1

HCID 178450851HCID 178450851, compound

Procedure

To a solution of [5-(2-Ethyl-6-methyl-phenoxy)-1,3-dioxo-1,3-dihydro-isoindol-2-yl]-acetic acid methyl ester (22 mmol, 7.77 g) in anhydrous n-butanol (150 mL) was added a 1 N solution of sodium in n-butanol (45 mmol, 45 mL) at 95° C. in one portion with stirring. Stirring was continued at 95° C. for 3 h before the mixture was concentrated in vacuo. To the residue was added 2 N hydrochloric acid (60 mmol, 30 mL) and EtOAc (150 mL) and the mixture was stirred vigorously for 45 min. Subsequently, the solid component was sucked off, washed with water and dried in vacuo to give the title compound as a tan solid (623 mg); MS-(+)-ion: M+1=396.5.

Workup

  1. stirringStirring
  2. concentrationwas concentrated in vacuo
  3. stirringthe mixture was stirred vigorously for 45 min
  4. washwashed with water
  5. customdried in vacuo

Sources & evidence

ORD record
ord-f34febd720484cb1b5dbc0b6899109c0
Source dataset
uspto-grants-2015_11
Patent number
US09174976B2

Reaction notes

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