Chloromethyl Methyl Ether → 4-(Methoxymethyloxy)-phenyldisulfide

HRID 1530890Notes

Reaction equation

HRID 1530890 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][S:9][C:10]2[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=2)=[CH:4][CH:3]=1.[H-].[Na+].Cl[CH2:20][O:21][CH3:22].[Cl-].[Na+].O.[C:26]([O:29][CH2:30]C)(=O)C>CN(C)C=O>[CH3:20][O:21][CH2:22][O:16][C:13]1[CH:14]=[CH:15][C:10]([S:9][S:8][C:5]2[CH:4]=[CH:3][C:2]([O:1][CH2:26][O:29][CH3:30])=[CH:7][CH:6]=2)=[CH:11][CH:12]=1

Participants

6

Reactant 4

HCID 7864Chloromethyl Methyl EtherHCID 24758Sodium hydrideHCID 2806654-[(4-Hydroxyphenyl)disulfanyl]phenolHCID 131718255Brine ethyl acetate

Product 1

HCID 882208684-(Methoxymethyloxy)-phenyldisulfide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-hydroxyphenyldisulfide (650 mg, 2.60 mmol) in 10 mL of anhydrous N,N-dimethylformamide at 10° C. was added sodium hydride (230 mg, 5.75 mmol, 60% dispersion in mineral oil . After stirring for 15 minutes, chloromethylmethyl ether (0.44 mL, 5.75 mmol) was added via syringe. The reaction was warmed to ambient temperature and stirred for 0.5 hours. The mixture was distributed between brine/ethyl acetate (20 mL each). The layers were separated and the aqueous phase extracted with ethyl acetate (2×20 mL). The organic was dried (sodium sulfate) and concentrated to a yellow oil (993 mg, 100%). An analytical sample of 4-(methoxymethyloxy)-phenyldisulfide was prepared by chromatography (silicon dioxide, 4% ethyl acetate/hexanes). 1H NMR (DMSO-d6) d 7.40 (d, J=6.9 Hz, 4H), 7.00 (d, J=6.9 Hz, 4H), 5.15 (s, 4H), 3.32 (s, 6H). FD mass spec: 338. Anal. Calcd. for C16H18O4S2: C, 56.78; H, 5.36. Found: C, 57.08; H, 5.44.

Workup

  1. stirringstirred for 0.5 hours
  2. customThe layers were separated
  3. extractionthe aqueous phase extracted with ethyl acetate (2×20 mL)
  4. dry with materialThe organic was dried (sodium sulfate)
  5. concentrationconcentrated to a yellow oil (993 mg, 100%)

Sources & evidence

ORD record
ord-835cbd3ce99c4b97a8e597c716be3ad2
Source dataset
uspto-grants-2001_03
Patent number
US06197790B1

Reaction notes

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