Hydrochloric Acid → Carbonic acid 2,2-dimethylbutyl ester 4-nitrophenyl ester

HRID 2089661Notes

Reaction equation

HRID 2089661 reaction equation
Cl[C:2]([O:4][C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][CH:6]=1)=[O:3].[CH3:14][C:15]([CH3:20])([CH2:18][CH3:19])[CH2:16][OH:17].ClCCl.Cl>C(OCC)(=O)C.N1C=CC=CC=1>[N+:11]([C:8]1[CH:7]=[CH:6][C:5]([O:4][C:2](=[O:3])[O:17][CH2:16][C:15]([CH3:20])([CH3:14])[CH2:18][CH3:19])=[CH:10][CH:9]=1)([O-:13])=[O:12]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6344DichloromethaneHCID 144542,2-DimethylbutanolHCID 821294-Nitrophenyl chloroformate

Product 1

HCID 67469959Carbonic acid 2,2-dimethylbutyl ester 4-nitrophenyl ester

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of 4-nitrophenyl chloroformate (1.97 g), 2,2-dimethylbutan-1-ol [CAS No. 1185-33-7] (1 g), and dichloromethane (30 mL), pyridine (1.58 mL) was added, and the resulting mixture was stirred at room temperature for 3 days. To the mixture, ethyl acetate and 1 N hydrochloric acid were added. After shaking the resulting mixture, the organic layer was collected, sequentially washed twice with water and with saturated aqueous sodium chloride solution, and dried over anhydrous sodium sulfate. The desiccant was filtered off, and the filtrate obtained was concentrated under reduced pressure. The residue obtained was purified by silica gel column chromatography (mixed solvent of heptane-ethyl acetate) to obtain the captioned compound (2.23 g).

Workup

  1. stirringAfter shaking the resulting mixture
  2. customthe organic layer was collected
  3. washsequentially washed twice with water and with saturated aqueous sodium chloride solution
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationThe desiccant was filtered off
  6. customthe filtrate obtained
  7. concentrationwas concentrated under reduced pressure
  8. customThe residue obtained
  9. customwas purified by silica gel column chromatography (mixed solvent of heptane-ethyl acetate)

Sources & evidence

ORD record
ord-7d22d57bdae741d0a19ad5c1099765c1
Source dataset
uspto-grants-2013_05
Patent number
US08436009B2

Reaction notes

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