2,4,6-Triisopropylphenol → HCID 53914629, compound

HRID 1721390Notes

Reaction equation

HRID 1721390 reaction equation
Cl[S:2]([CH2:5][C:6]([O:8][CH2:9][CH3:10])=[O:7])(=[O:4])=[O:3].[CH:11]([C:14]1[CH:19]=[C:18]([CH:20]([CH3:22])[CH3:21])[CH:17]=[C:16]([CH:23]([CH3:25])[CH3:24])[C:15]=1[OH:26])([CH3:13])[CH3:12]>C(Cl)Cl>[CH:23]([C:16]1[CH:17]=[C:18]([CH:20]([CH3:22])[CH3:21])[CH:19]=[C:14]([CH:11]([CH3:13])[CH3:12])[C:15]=1[O:26][S:2]([CH2:5][C:6]([O:8][CH2:9][CH3:10])=[O:7])(=[O:4])=[O:3])([CH3:25])[CH3:24]

Participants

4

Reactant 2

HCID 821582,4,6-TriisopropylphenolHCID 12225100Ethyl (chlorosulfonyl)acetate

Product 1

HCID 53914629HCID 53914629, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

1H NMR (CDCl3): δ1.35 (t, 3H), 4.1 (s, 2H), 4.25 (q, 2H). A mixture of ethyl sulfoacetate (16.82 g, 100 mM) and POCl3 (30.67 g, 200 mM) was heated at 125° C. for 5 hours. The mixture was cooled and filtered, and excess POCl3 was removed to give ethyl chlorosulfonylacetate. The ethyl chlorosulfonylacetate (18.66 g, 100 mM) was added dropwise with stirring to a solution of 2,4,6-triisopropylphenol (22.1 g, 100 mM) in 50 mL CH2Cl2 maintained at 0° C. The mixture was stirred at room temperature for an additional 18 hours. The solvent was removed and the residue was redissolved in 100 mL ethyl acetate and washed with 1 N HCl and brine. The ethyl acetate was evaporated to provide ethyl (2,4,6-triisopropylphenoxysulfonyl)acetate.

Workup

  1. customThe solvent was removed
  2. dissolutionthe residue was redissolved in 100 mL ethyl acetate
  3. washwashed with 1 N HCl and brine
  4. customThe ethyl acetate was evaporated

Sources & evidence

ORD record
ord-d15e557318d141948398b8e98962a899
Source dataset
uspto-grants-1996_04
Patent number
US05510379

Reaction notes

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