Water → HCID 18652760, compound

HRID 1033129Notes

Reaction equation

HRID 1033129 reaction equation
[CH3:1][C@@H:2]([CH2:5][CH3:6])[CH2:3][OH:4].[CH3:7][C:8]1[CH:16]=[CH:15][C:11]([C:12](Cl)=[O:13])=[CH:10][CH:9]=1.O.C1(C)C=CC=CC=1>N1C=CC=CC=1>[CH3:1][C@@H:2]([CH2:5][CH3:6])[CH2:3][O:4][C:12](=[O:13])[C:11]1[CH:15]=[CH:16][C:8]([CH3:7])=[CH:9][CH:10]=1

Participants

6

Reactant 4

HCID 962WaterHCID 1140TolueneHCID 134054-Methylbenzoyl ChlorideHCID 2723602(S)-2-methyl-1-butanol

Product 1

HCID 18652760HCID 18652760, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

28.51 g (0.23 moles) of a commercially available (S)-2-methylbutanol was dissolved in 100 ml of pyridine. The mixture was cooled and 50 g (0.23 moles) of a commercially available 4-methylbenzoic chloride was added thereto while cooling. The mixture was then allowed to react with stirring at 50° to 60° C. for 2 hours. On completion of the reaction, 300 ml of water and 300 ml of toluene were added, and after vigorous stirring, the toluene layer was separated out and washed with 6N HCl. Washing was continued until this layer was neutral. This toluene layer was dried with anhydrous magnesium sulfate after which the toluene was distilled away. The residue was further subjected to evaporation under reduced pressure at 118° to 120° C. (5 mm Hg) and the distillate recovered, whereby 59.61 g of the objective 4-methylbenzoic((S)-2-methylbutyl) ester was obtained.

Workup

  1. temperatureThe mixture was cooled
  2. temperaturewhile cooling
  3. customto react
  4. additionwere added
  5. customafter vigorous stirring, the toluene layer was separated out and
  6. washwashed with 6N HCl
  7. washWashing
  8. dry with materialThis toluene layer was dried with anhydrous magnesium sulfate after which the toluene
  9. distillationwas distilled away
  10. customThe residue was further subjected to evaporation under reduced pressure at 118° to 120° C. (5 mm Hg)
  11. distillationthe distillate recovered

Sources & evidence

ORD record
ord-b591cc98a6264919b92f88ce5ee1f390
Source dataset
uspto-grants-1994_05
Patent number
US05310503

Reaction notes

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