Guaiacol → HCID 1729096, compound

HRID 2280183Notes

Reaction equation

HRID 2280183 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[OH:9].C(N(CC)CC)C.[CH3:17][S:18](Cl)(=[O:20])=[O:19]>ClCCl>[CH3:17][S:18]([O:9][C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=1[O:2][CH3:1])(=[O:20])=[O:19]

Participants

5

Reactant 3

HCID 460GuaiacolHCID 8471TriethylamineHCID 31297Methanesulfonyl chloride

Product 1

HCID 1729096HCID 1729096, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 2-methoxyphenol (50 g, 402.8 mmol) and triethylamine (84.2 mL, 604.2 mmol) in anhydrous dichloromethane (300 mL), was added methanesulfonyl chloride (37.6 mL, 483.3 mmol) at 0° C. under nitrogen. The reaction mixture was stirred at 0° C. for 2 hours, quenched with ice water (250 mL) and transferred to a separatory funnel. The organic phase was washed with a solution of NaOH (8 g) in ice water (200 mL), brine, dried over Na2SO4, filtered and concentrated under reduced pressure to give the title compound as a colorless liquid (81.44 g, 100%). 1H NMR (400 MHz, DMSO-d6) δ 3.32 (s, 3H), 3.83 (s, 3H), 6.96-7.0 (m, 1H), 7.18-7.2 (m, 1H), 7.27-7.33 (m, 2H).

Workup

  1. customquenched with ice water (250 mL)
  2. customtransferred to a separatory funnel
  3. washThe organic phase was washed with a solution of NaOH (8 g) in ice water (200 mL), brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-a20e90d4794d40b4a32afcdd9c5db0df
Source dataset
uspto-grants-2015_09
Patent number
US09138013B2

Reaction notes

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