Hydrochloric Acid → HCID 59608829, compound

HRID 454788Notes

Reaction equation

HRID 454788 reaction equation
Cl[C:2](Cl)([O:4][C:5](=[O:11])[O:6][C:7](Cl)(Cl)Cl)Cl.[CH2:13]([C:15](CO)(C)[C:16]([O:18][CH2:19][CH3:20])=[O:17])O.N1C=CC=CC=1.C(=O)=O.CC(C)=O.[NH4+].[Cl-].Cl.C([O-])(O)=O.[Na+]>C(Cl)Cl.[Cl-].[Na+].O.O>[CH3:13][C:15]1([C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH2:7][O:6][C:5](=[O:11])[O:4][CH2:2]1

Participants

11

Reactant 7

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 25517Ammonium ChlorideHCID 94429Triphosgene2×HCID 516892Sodium BicarbonateHCID 18522661Acetone cardiceHCID 23370761Ethyl 3-hydroxy-2-(hydroxymethyl)-2-methylpropanoate

Product 1

HCID 59608829HCID 59608829, compoundYield 112.8%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×HCID 57417360Sodium chloride; waterSolvent

Procedure

A solution of triphosgene (19.5 g, 0.065 mol) in CH2Cl2 (200 mL) was added stepwise to a CH2Cl2 solution (150 mL) of ethyl 2,2-bis(methylol)propionate (EtMPA) (21.1 g, 0.131 mol) and pyridine (64 mL, 0.786 mol) over 30 min at −75° C. with dry ice/acetone. The reaction mixture was kept stirring for another 2 hours under chilled condition and then allowed to heat to room temperature. Saturated NH4Cl aqueous solution (200 mL) was added to the reaction mixture to decompose excess triphosgene. The organic phase was then treated with 1 N HCl aq (200 mL), followed by saturated NaHCO3 (200 mL), brine (200 mL), and water (200 mL). After the CH2Cl2 solution was dried over MgSO4 and evaporated, the residue was recrystallized from ethyl acetate to give white crystals (13.8 g, 56%). 1H NMR: delta 4.68 (d, 2H, CH2OCOO), 4.25 (q, 1H, OCH2CH3), 4.19 (d, 2H, CH2OCOO), 1.32 (s, 3H, CH3), 1.29 (t, 3H, CH3CH2O). 13C NMR: delta 171.0, 147.5, 72.9, 62.1, 39.9, 17.3, 13.8. HR-ESI-MS: m/z calcd for C8H12O5; Na, 211.0582; found, 221.0578.

Workup

  1. temperatureunder chilled condition
  2. dry with materialAfter the CH2Cl2 solution was dried over MgSO4
  3. customevaporated
  4. customthe residue was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-1e3588c5ac25433881e9aae035540aa4
Source dataset
uspto-grants-2013_07
Patent number
US08496946B2

Reaction notes

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