tert-Butanol → tert-Butyl (4-methylphenyl)acetate

HRID 1955726Notes

Reaction equation

HRID 1955726 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=[O:10])=[CH:4][CH:3]=1.[C:12](O)([CH3:15])([CH3:14])[CH3:13].CN(C1C=CC=CN=1)C.C1(N=C=NC2CCCCC2)CCCCC1>ClCCl>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 6386tert-ButanolHCID 10868DicyclohexylcarbodiimideHCID 218852-DimethylaminopyridineHCID 248474p-Tolylacetic acid

Product 1

HCID 12362014tert-Butyl (4-methylphenyl)acetate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
25 °C

Procedure

450 g (3 mol) of 4-methylphenylacetic acid, 1.13 l (12 mol) of tert-butanol and 90 g (0.74 mol) of dimethylaminopyridine are dissolved in 2 l of dichloromethane. After addition of 680 g (3.3 mol) of dicyclohexylcarbodiimide, dissolved in 400 ml of dichloromethane, the mixture is stirred at 25° C. for 20 h, the precipitated urea is filtered off with suction and washed with 200 ml of dichloromethane, and the organic phase is washed twice each with 500 ml of 2N hydrochloric acid and water. The organic phase is concentrated and distilled.

Workup

  1. filtrationthe precipitated urea is filtered off with suction
  2. washwashed with 200 ml of dichloromethane
  3. washthe organic phase is washed twice each with 500 ml of 2N hydrochloric acid and water
  4. concentrationThe organic phase is concentrated
  5. distillationdistilled

Sources & evidence

ORD record
ord-152b12b930ed42f7995bd01041dfbeb7
Source dataset
uspto-grants-1998_07
Patent number
US05776964

Reaction notes

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