Water → 4-methylbenzoic acid [(R)-2-methylheptyl]ester

HRID 483902

Reaction equation

HRID 483902 reaction equation
C[C@@H:2](O)[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[CH3:10][C:11]1[CH:19]=[CH:18][C:14]([C:15](Cl)=[O:16])=[CH:13][CH:12]=1.[OH2:20].[C:21]1(C)C=CC=CC=1>N1C=CC=CC=1>[CH3:21][C@H:7]([CH2:6][CH2:5][CH2:4][CH2:3][CH3:2])[CH2:8][O:20][C:15](=[O:16])[C:14]1[CH:18]=[CH:19][C:11]([CH3:10])=[CH:12][CH:13]=1

Participants

6

Reactant 4

HCID 962WaterHCID 1140TolueneHCID 134054-Methylbenzoyl ChlorideHCID 80080(R)-2-Octanol

Product 1

HCID 540413924-methylbenzoic acid [(R)-2-methylheptyl]ester

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

40 g (0.31 moles) of a commercially available (R)-2-octanol was dissolved in 100 ml of pyridine. The mixture was cooled and 47.93 g (0.31 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 144° to 146° C. (2 mm Hg) and the distillate recovered, whereby 70.37 g of the objective 4-methylbenzoic acid [(R)-2-methylheptyl]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
  9. distillationafter which the toluene was distilled away
  10. customThe residue was further subjected to evaporation under reduced pressure at 144° to 146° C. (2 mm Hg)
  11. distillationthe distillate recovered

Sources & evidence

ORD record
ord-9e291465847147e39d44b0f7d0979f3e
Source dataset
uspto-grants-1993_07
Patent number
US05227512

Linked notes

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