Benzyl mercaptan → HCID 53788762, compound

HRID 918007Notes

Reaction equation

HRID 918007 reaction equation
Br[CH2:2][C:3]([CH3:16])=[CH:4][CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([C:13](=[O:15])[CH3:14])=[CH:9][CH:8]=1.[Na].[CH2:18]([SH:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>CN(C)C=O>[CH2:18]([S:25][CH2:2][C:3]([CH3:16])=[CH:4][CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([C:13](=[O:15])[CH3:14])=[CH:9][CH:8]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 7509Benzyl mercaptanHCID 5360545SodiumHCID 54204927HCID 54204927, compound

Product 1

HCID 53788762HCID 53788762, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

14.15 g (0.05 mol) of 4'-(4-bromo-3-methyl-2-butenyloxy)- acetophenone are added at 10°-15° during the course of 1 hour to 7.3 g (0.05 mol) of sodium salt of benzylmercaptan which is dissolved in 120 cc of dimethylformamide. The mixture is stirred at 20°-25° for 20 hours, is subsequently filtered and the filtrate is evaporated at reduced pressure. The residue is dissolved in ether, is extracted with saturated salt solution and the ether solution is evaporated. The remaining yellowish oil is chromatographed on silica gel with hexane/ethyl acetate 2:1. After recrystallization from ether/hexane the 4'-(4-benzylthio-3-methyl-2-butenyloxy)-acetophenone is obtained as colourless crystals. M.P. 75°-76.5°.

Workup

  1. filtrationis subsequently filtered
  2. customthe filtrate is evaporated at reduced pressure
  3. dissolutionThe residue is dissolved in ether
  4. extractionis extracted with saturated salt solution
  5. customthe ether solution is evaporated
  6. customThe remaining yellowish oil is chromatographed on silica gel with hexane/ethyl acetate 2:1
  7. customAfter recrystallization from ether/hexane the 4'-(4-benzylthio-3-methyl-2-butenyloxy)-acetophenone
  8. customis obtained as colourless crystals

Sources & evidence

ORD record
ord-52506e6339214e04b2637b7958812027
Source dataset
uspto-grants-1976_07
Patent number
US03968235

Reaction notes

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