Water → 2-isopropyl-phenyl acetate

HRID 866015Notes

Reaction equation

HRID 866015 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 mol). This solution is cooled to -12° and to this is added acetyl chloride (3.15 kg, 40.2 mol) 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 (12 L). After separation of the layers the organic layer is further washed with water (2×12 L) 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 (2×12 L)
  8. customevaporated in vacuo (50°, 2 Torr)

Sources & evidence

ORD record
ord-7572de154fff4b1ca8d79ab610af3489
Source dataset
uspto-grants-1996_10
Patent number
US05569674

Reaction notes

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