Ethanol → 127164-89-0

HRID 330340Notes

Reaction equation

HRID 330340 reaction equation
C(OC1C=CC([CH:11]([S:16][CH:17]([C:22]2C=CC(OC(=O)C)=CC=2)[CH:18]=[C:19](C)C)[CH:12]=[C:13]([CH3:15])[CH3:14])=CC=1)(=O)C.O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O.[OH-].[K+].[CH2:48]([OH:50])[CH3:49]>P(=O)(O)(O)O.O>[CH3:15][C:13]1([CH3:14])[C:18]2[C:17](=[CH:22][CH:49]=[C:48]([OH:50])[CH:19]=2)[S:16][CH2:11][CH2:12]1

Participants

7

Reactant 4

HCID 702EthanolHCID 14797Potassium HydroxideHCID 14812Phosphorus oxide (P4O10)HCID 54068677HCID 54068677, compound

Product 1

HCID 19834253127164-89-0

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 1004Phosphoric AcidSolvent

Procedure

A mixture of 6.8 g (0.029 mmol) of 4-acetoxyphenyl-3-methylbut-2-enylsulfide and 17 g of 1:10 (w/w) phosphorus pentoxide in phosphoric acid was stirred at room temperature under nitrogen for 15hours. The reaction mixture was then treated with water and stirred for 40 min. The mixture was then extracted with 2×50 ml ether. The ether extracts were combined and the solvent removed in-vacuo. The residue was then stirred under nitrogen with a solution of 1.93 g (0.034 mmol) of potassium hydroxide in 6 ml of water and 12 ml of ethanol for 1 hour. The ethanol was then removed from the mixture on the rotary evaporator and the aqueous solution then acidified to PH-2 with sulfuric acid. The acidified solution was extracted with 2×50 ml ether. The ether extracts were combined and washed successively with water and saturated NaCl solution and then dried (MgSO4). The ether solution was then filtered and the solvent removed in-vacuo. The resultant crude product was purified by flash chromatography (silica; 20% ethyl acetate in hexanes) to give the title compound as a colorless, low-melting solid. PMR (CDCl3): 6 1.25 (6H, s), 1.90 (2H, m), 2.97 (2H, m), 6.57 (1H, dd, J~8.6, 2.7 Hz), 6.88 (1H, d, J~2.7 Hz), 6.90 (1H, d, J~8.6 Hz).

Workup

  1. stirringstirred for 40 min
  2. extractionThe mixture was then extracted with 2×50 ml ether
  3. customthe solvent removed in-vacuo
  4. customThe ethanol was then removed from the mixture on the rotary evaporator
  5. extractionThe acidified solution was extracted with 2×50 ml ether
  6. washwashed successively with water and saturated NaCl solution
  7. dry with materialdried (MgSO4)
  8. filtrationThe ether solution was then filtered
  9. customthe solvent removed in-vacuo
  10. customThe resultant crude product was purified by flash chromatography (silica; 20% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-124c3e5764c5406c9b4b9d59acaa3135
Source dataset
uspto-grants-1990_01
Patent number
US04895868

Reaction notes

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