Water → 2-isopropyl-phenyl acetate

HRID 1609732Notes

Reaction equation

HRID 1609732 reaction equation
[CH:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[OH:10])([CH3:3])[CH3:2].C(N(CC)CC)C.[C:18](Cl)(=[O:20])[CH3:19].O>C(OCC)(=O)C>[C:18]([O:10][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=1[CH:1]([CH3:3])[CH3:2])(=[O:20])[CH3:19]

Participants

6

Reactant 4

HCID 962WaterHCID 6367Acetyl chlorideHCID 69432-IsopropylphenolHCID 8471Triethylamine

Product 1

HCID 3462332-isopropyl-phenyl acetate

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

2-Isopropylphenol (5.0 kg, 36.7 mol) is dissolved in ethyl acetate (20.8 L) and to this is added triethylamine (4.48 kg, 44.1 mmol). This solution is cooled to -12° and to this is added acetyl chloride (3.15 kg, 40.2 tool) over a period of 2.5 hours keeping the temperature below -10°. Triethylamine hydrochloride precipitates immediately. After the addition is complete stirring is continued for 1 hour at 15° at which time a solid mass is formed. This is dissolved by the addition of water (12L). After separation of the layers the organic layer is further washed with water (233 12L) and evaporated in vacuo (50°, 2 Torr) and then at 70°, 2 Torr to give 2-isopropyl-phenyl acetate as a residual amber oil.

Workup

  1. temperatureThis solution is cooled to -12°
  2. customthe temperature below -10°
  3. customTriethylamine hydrochloride precipitates immediately
  4. additionAfter the addition
  5. customa solid mass is formed
  6. customAfter separation of the layers the organic layer
  7. washis further washed with water (233 12L)
  8. customevaporated in vacuo (50°, 2 Torr)

Sources & evidence

ORD record
ord-c881b72bff8d493396c44d844ade62e1
Source dataset
uspto-grants-1995_03
Patent number
US05401772

Reaction notes

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