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

HRID 1066761Notes

Reaction equation

HRID 1066761 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].C(N(C1C=CN=CC=1)CC)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 248474p-Tolylacetic acidHCID 117687514-Diethylaminopyridine

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-methylphenyl-acetic acid (Aldrich), 1.13 l (12 mol) of tert-butanol and 90 g (0.74 mol) of 4-(N,N-diethylamino)pyridine 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 2 M 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 2 M hydrochloric acid and water
  4. concentrationThe organic phase is concentrated
  5. distillationdistilled

Sources & evidence

ORD record
ord-b21a3f78409b4b97a18674c91ff231f6
Source dataset
uspto-grants-2001_06
Patent number
US06245775B1

Reaction notes

Loading…