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

HRID 636462
Notes
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Reaction equation

HRID 636462 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

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 6344Dichloromethane
Solvent
2×

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 2M hydrochloric acid and water. The organic phase is dried using sodium sulphate, 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 2M hydrochloric acid and water
  4. customThe organic phase is dried
  5. concentrationconcentrated
  6. distillationdistilled

Sources & evidence

ORD record
ord-3ea04fe0288045e8a8ddbb04ad8ed205
Source dataset
uspto-grants-2001_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06194424B1

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes