Hydrochloric Acid → HCID 21190285, compound

HRID 619457Notes

Reaction equation

HRID 619457 reaction equation
[CH3:1][C:2]([CH3:28])([CH2:16][CH2:17][O:18]COCC1C=CC=CC=1)[CH2:3][CH2:4][C:5]12[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]1[C:9](=[O:15])[NH:8][C:6]2=[O:7].Cl>CO>[CH3:1][C:2]([CH3:28])([CH2:16][CH2:17][OH:18])[CH2:3][CH2:4][C:5]12[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]1[C:9](=[O:15])[NH:8][C:6]2=[O:7]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 21190108HCID 21190108, compound

Product 1

HCID 21190285HCID 21190285, compoundYield 93.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 5.70 g (14.9 mmol) of 1-(3,3-dimethyl-5-benzyloxymethoxypentyl)phthalimide in 70 ml of methanol was added 3.75 ml (45 mmol) of conc. HCl. The mixture was stirred for 3 hours at 60° C. The reaction mixture was cooled, and the solvent was distilled off. The residue was dissolved in 100 ml of water, to which was added 30 ml of 1N aqueous solution of sodium hydroxide. The mixture was extracted with dichloromethane. The extract solution was dried, and the solvent was distilled off. The residue was purified by column chromatography (eluent: n-hexane/ethyl acetate=2:1→1:2) to give 3.63 g of the desired compound (93.2%, white solid).

Workup

  1. temperatureThe reaction mixture was cooled
  2. distillationthe solvent was distilled off
  3. dissolutionThe residue was dissolved in 100 ml of water, to which
  4. additionwas added 30 ml of 1N aqueous solution of sodium hydroxide
  5. extractionThe mixture was extracted with dichloromethane
  6. customThe extract solution was dried
  7. distillationthe solvent was distilled off
  8. customThe residue was purified by column chromatography (eluent: n-hexane/ethyl acetate=2:1→1:2)

Sources & evidence

ORD record
ord-75004f0b6b5444a7b6429c4b4d8a96b6
Source dataset
uspto-grants-1999_09
Patent number
US05958942

Reaction notes

Loading…