4-Methoxy-alpha-toluenethiol → HCID 21924853, compound

HRID 347295Notes

Reaction equation

HRID 347295 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH2:7][SH:8])=[CH:5][CH:4]=1.C[O-].Br[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][OH:26]>CO>[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH2:7][S:8][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][OH:26])=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 804074-Methoxy-alpha-toluenethiolHCID 13789512-Bromo-1-dodecanolHCID 3826051Methoxide

Product 1

HCID 21924853HCID 21924853, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Na (800 mg, 34.8 mmol) was dissolved in 30 mL of dry MeOH. Under argon, p-methoxybenzylmercaptan (2.75 mL, 3.04 g, 19.7 mmol) was added to the methoxide solution. After a few minutes, 12-bromododecanol (2.5 g, 9.43 mmol) was dropped into the reaction mixture. Within 5 minutes a solid began to come out of solution. After a minimum of 3 h, the reaction was filtered and washed 3× with cold MeOH, yielding 2.874 g (8.49 mmol, 90%) of pure product after drying. 1H NMR (CDCl3): d 7.23 (d, J=8.8 Hz, 2H, AA′ of AA′ BB′ aromatic system), 6.85 (d, J=8.8 Hz, 2H, BB′ of AA′ BB′ aromatic system), 3.80 (s, 3H, methoxy), 3.66 (s, 2H, benzyl), 3.64 (dt, J1=6.6 Hz, J2=5.5 Hz, 2H, RCH2OH), 2.40 (t, J=7.3 Hz, 2H, RSCH2R), 1.50–1.65 (cm, 4H, CH2 b to heteroatoms), 1.2–1.4 (cm, 16H, bulk methylenes).

Workup

  1. waitAfter a few minutes
  2. filtrationAfter a minimum of 3 h, the reaction was filtered
  3. washwashed 3× with cold MeOH

Sources & evidence

ORD record
ord-96b3cf9eec9341c2a75d9f25788a4a8a
Source dataset
uspto-grants-2007_02
Patent number
US07173130B2

Reaction notes

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