Water → HCID 59410128, compound

HRID 1805116Notes

Reaction equation

HRID 1805116 reaction equation
[C:1]([C:5]1[CH:10]=[C:9]([CH2:11][CH3:12])[CH:8]=[CH:7][C:6]=1[OH:13])([CH3:4])([CH3:3])[CH3:2].CCN(CC)CC.Cl[C:22]([O:24][CH3:25])=[O:23].O>C(Cl)Cl>[C:22](=[O:23])([O:24][CH3:25])[O:13][C:6]1[CH:7]=[CH:8][C:9]([CH2:11][CH3:12])=[CH:10][C:5]=1[C:1]([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 6586Methyl chloroformateHCID 73092-tert-Butyl-4-ethylphenolHCID 8471Triethylamine

Product 1

HCID 59410128HCID 59410128, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-tert-butyl-4-ethyl-phenol (10 g, 56.1 mmol) in DCM (50 mL) was added Et3N (17 g, 168.0 mmol) and methyl chloroformate (11 g, 116.4 mmol) at 0° C. The mixture was stirred overnight at room temperature. Water was added to quench the reaction and the mixture was extracted with EtOAc (200 mL×3). The combined organic layers were dried over anhydrous Na2SO4, filtered and evaporated under vacuum to give 2-tert-butyl-4-ethylphenyl methyl carbonate (12 g, 91%). 1H NMR (300 MHz, CDCl3), 7.06-7.02 (m, 2H), 7.02 (s, 1H), 3.92 (s, 3H), 2.64 (q, J=7.5 Hz, 2H), 1.37 (s, 9H), 1.54 (t, J=7.5 Hz, 3H)

Workup

  1. customto quench
  2. customthe reaction
  3. extractionthe mixture was extracted with EtOAc (200 mL×3)
  4. dry with materialThe combined organic layers were dried over anhydrous Na2SO4
  5. filtrationfiltered
  6. customevaporated under vacuum

Sources & evidence

ORD record
ord-d8c0528a35b845e6b5d7d5ca95fb3ef6
Source dataset
uspto-grants-2013_01
Patent number
US08354427B2

Reaction notes

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