Hydrochloric Acid → HCID 15177066, compound

HRID 976049Notes

Reaction equation

HRID 976049 reaction equation
[C:1]1([CH2:11][C:12]([CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)(C(OC(C)(C)C)=O)[C:13]([O:15]C(C)(C)C)=[O:14])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.Cl>C1COCC1>[C:1]1([CH2:11][CH:12]([CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C:13]([OH:15])=[O:14])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 53819314HCID 53819314, compound

Product 1

HCID 15177066HCID 15177066, compoundYield 82.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
2000 °C

Procedure

A solution of 20.0 g (0.045 mol) of di-t-butyl (1-naphthylmethyl)benzylmalonate in 350 mL THF was treated repeatedly with HCl gas over a 3-hour period. The solvent was removed under reduced pressure and the residue heated at 2000° C. for 25 minutes. The residue was taken up in Et2O and extracted with 1N NaOH. The NaOH solution was acidified with dilute HCl and extracted with Et2O. The Et2O was washed with saturated NaCl, dried over MgSO4, and the solvent removed under reduced pressure leaving 10.78 g (82% yield) of the product as a white solid. The structure was confirmed by NMR and mass spectroscopy.

Workup

  1. customThe solvent was removed under reduced pressure
  2. extractionextracted with 1N NaOH
  3. extractionextracted with Et2O
  4. washThe Et2O was washed with saturated NaCl
  5. dry with materialdried over MgSO4
  6. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-3eb4cd0fa7ea482185e11025d225126e
Source dataset
uspto-grants-1997_03
Patent number
US05610177

Reaction notes

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