Methanesulfonyl chloride → Methanesulfonic acid 1-methyl-2-(1-phenyl-2,5-cyclohexadien-1-yl)-ethyl ester

HRID 2287125Notes

Reaction equation

HRID 2287125 reaction equation
[CH3:1][CH:2]([OH:16])[CH2:3][C:4]1([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:9]=[CH:8][CH2:7][CH:6]=[CH:5]1.[S:17](Cl)([CH3:20])(=[O:19])=[O:18]>N1C=CC=CC=1>[CH3:1][CH:2]([O:16][S:17]([CH3:20])(=[O:19])=[O:18])[CH2:3][C:4]1([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:5]=[CH:6][CH2:7][CH:8]=[CH:9]1

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 23459447alpha-Methyl-1-phenyl-2,5-cyclohexadien-1-ethanol

Product 1

HCID 53747931Methanesulfonic acid 1-methyl-2-(1-phenyl-2,5-cyclohexadien-1-yl)-ethyl ester

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

8 g. of α-methyl-1-phenyl-2,5-cyclohexadien-1-ethanol are dissolved in 50 ml. of pyridine and 6.4 g. of mesyl chloride are added dropwise at 0°-5° C. After stirring at room temperature for 2 hours, the mixture is worked-up as follows: The mixture is treated with ice-water and extracted with ether. The ether phase is washed with 3 N aqueous hydrochloric acid, then washed neutral, dried and concentrated. The crude product obtained is chromatographed on 100 g. of silica gel with ether/petroleum ether (1:1). There is obtained an oily product which crystallizes in the cold. After crystallization from methylene chloride/hexane, there is obtained methanesulfonic acid 1-methyl-2-(1-phenyl-2,5-cyclohexadien-1-yl)-ethyl ester having a melting point of 51°-53° C.

Workup

  1. extractionextracted with ether
  2. washThe ether phase is washed with 3 N aqueous hydrochloric acid
  3. washwashed neutral
  4. customdried
  5. concentrationconcentrated
  6. customThe crude product obtained
  7. customis chromatographed on 100 g
  8. customThere is obtained an oily product which
  9. customcrystallizes in the cold
  10. customAfter crystallization from methylene chloride/hexane

Sources & evidence

ORD record
ord-f7b1015871e149a2997297cc98245691
Source dataset
uspto-grants-1981_05
Patent number
US04269788

Reaction notes

Loading…