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

HRID 1457615Notes

Reaction equation

HRID 1457615 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].C1(N=C=NC2CCCCC2)CCCCC1>CN(C1C=CN=CC=1)C.C(Cl)Cl>[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 3

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

Product 1

HCID 12362014tert-Butyl (4-methylphenyl)acetate

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 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-dimethylamino)pyridine are dissolved in 2 l of methylene chloride. After addition of 680 g (3.3 mol) of dicyclohexylcarbodiimide, dissolved in 400 ml of methylene chloride, the mixture is stirred at 25° C. for 20 hours, the urea which has precipitated out is filtered off with suction and washed with 200 ml of methylene chloride and the organic phase is washed in each case twice with 500 ml of 2M hydrochloric acid and water. The organic phase is concentrated and distilled. Yield: 408 g (66% of theory) Boiling point: 73°-78° C./0.2 mm

Workup

  1. customthe urea which has precipitated out
  2. filtrationis filtered off with suction
  3. washwashed with 200 ml of methylene chloride
  4. washthe organic phase is washed in each case twice with 500 ml of 2M hydrochloric acid and water
  5. concentrationThe organic phase is concentrated
  6. distillationdistilled

Sources & evidence

ORD record
ord-4c599c4a5d234331947a139babc0986b
Source dataset
uspto-grants-1998_12
Patent number
US05849751

Reaction notes

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