Water → Menthyl bromoacetate

HRID 278527Notes

Reaction equation

HRID 278527 reaction equation
[CH:1]1([CH3:11])[CH2:6][CH2:5][CH:4]([CH:7]([CH3:9])[CH3:8])[CH:3]([OH:10])[CH2:2]1.[Br:12][CH2:13][C:14](O)=[O:15].O>C1(C)C=CC=CC=1>[Br:12][CH2:13][C:14]([O:10][CH:3]1[CH:4]([CH:7]([CH3:8])[CH3:9])[CH2:5][CH2:6][CH:1]([CH3:11])[CH2:2]1)=[O:15]

Participants

5

Reactant 3

HCID 962WaterHCID 1254MentholHCID 6227Bromoacetic Acid

Product 1

HCID 5152975Menthyl bromoacetate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

For the first stage, a solution of (−)-menthol (1.56 g, 10 mmol), 2-bromoacetic acid (1.39 g, 10 mmol) and monohydrated p-toluenesulphonic acid (0.5 g, 2.6 mmol) was brought to reflux for 3 h in 100 ml toluene. The water given off during the reaction is separated by azeotropic distillation. 100 ml toluene is added, and the mixture is washed 3 times with 10 ml of a 5% NaOH solution, then twice with 100 ml of brine, the organic solvent is dried on Na2SO4 and the solvent evaporated under vacuum. The menthyl 2-bromoacetate obtained (2.45 g, 89%) is used in the next step without purification.

Workup

  1. customis separated by azeotropic distillation
  2. addition100 ml toluene is added
  3. washthe mixture is washed 3 times with 10 ml of a 5% NaOH solution
  4. dry with materialtwice with 100 ml of brine, the organic solvent is dried on Na2SO4
  5. customthe solvent evaporated under vacuum

Sources & evidence

ORD record
ord-2f1872b93cf045d2be4ab7079b21bedf
Source dataset
uspto-grants-2002_03
Patent number
US06359168B1

Reaction notes

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