Monobenzone → HCID 86625878, compound

HRID 2421989Notes

Reaction equation

HRID 2421989 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:16][S:17](Cl)(=[O:19])=[O:18]>C(Cl)Cl>[CH3:16][S:17]([O:15][C:12]1[CH:11]=[CH:10][C:9]([O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[CH:14][CH:13]=1)(=[O:19])=[O:18]

Participants

4

Reactant 2

HCID 7638MonobenzoneHCID 31297Methanesulfonyl chloride

Product 1

HCID 86625878HCID 86625878, compoundYield 95.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-(Benzyloxy)phenol (4.00 g, 19.98 mmol) was dissolved in dry DCM (80 mL) under nitrogen atmosphere and cooled in an ice-water bath. Methanesulfonyl chloride (2.75 g, 23.97 mmol) was added during stirring followed by TEA (3.03 g, 29.96 mmol). The reaction mixture was stirred at rt for 2 h and then washed with saturated aqueous NaHCO3, dried (MgSO4), filtered and evaporated affording the title compound (5.32 g, 95.6%). 1H NMR (500 MHz, CDCl3): δ 3.13 (s, 3H), 5.08 (s, 2H), 7.01 (m, 2H), 7.23 (m, 2H), 7.35-7.45 (m, 5H).

Workup

  1. temperaturecooled in an ice-water bath
  2. stirringThe reaction mixture was stirred at rt for 2 h
  3. washwashed with saturated aqueous NaHCO3
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-5c4166578ebf4d1ba4ca46722188e353
Source dataset
uspto-grants-2011_06
Patent number
US07960380B2

Reaction notes

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