Sodium Hydroxide → HCID 18992122, compound

HRID 1776519Notes

Reaction equation

HRID 1776519 reaction equation
[C:1]([O:20][CH2:21][CH2:22][C:23]([O:25]C(C)(C)C)=[O:24])([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+]>C(O)C>[C:1]([O:20][CH2:21][CH2:22][C:23]([OH:25])=[O:24])([C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 86679475HCID 86679475, compound

Product 1

HCID 18992122HCID 18992122, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of tert-butyl 3-(trityloxy)propanoate (3.5 g, 9.01 mmol) and 6M NaOH (3.00 ml, 18.02 mmol) in ethanol was heated to reflux for 3 hours. After cooling the solvent was removed under vacuum and the residue was partitioned between DCM and aqueous 3% citric acid. The organic layer was washed with brine dried over Na2SO4. The solvent was evaporated and the crude was triturated with iPr2O and filtered affording 3-(trityloxy)propanoic acid (2.3 g, 6.92 mmol, 77% yield).

Workup

  1. temperatureto reflux for 3 hours
  2. temperatureAfter cooling the solvent
  3. customwas removed under vacuum
  4. customthe residue was partitioned between DCM and aqueous 3% citric acid
  5. washThe organic layer was washed with brine
  6. dry with materialdried over Na2SO4
  7. customThe solvent was evaporated
  8. customthe crude was triturated with iPr2O
  9. filtrationfiltered

Sources & evidence

ORD record
ord-c0cdc248a36141c8a6b54e4152ccc040
Source dataset
uspto-grants-2016_02
Patent number
US09265768B2

Reaction notes

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