(4-Chlorophenyl)acetic acid → (4-Chlorophenyl)acetic acid tert-butyl ester

HRID 22932

Reaction equation

HRID 22932 reaction equation
C([O:5][CH:6]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])N(C)C)(C)(C)C.[Cl:15][C:16]1[CH:21]=[CH:20][C:19]([CH2:22]C(O)=O)=[CH:18][CH:17]=1>C1(C)C=CC=CC=1.CCOC(C)=O>[C:11]([O:10][C:6](=[O:5])[CH2:22][C:19]1[CH:20]=[CH:21][C:16]([Cl:15])=[CH:17][CH:18]=1)([CH3:12])([CH3:13])[CH3:14]

Participants

5

Reactant 2

HCID 15880(4-Chlorophenyl)acetic acidHCID 5477121,1-bis(1,1-dimethylethoxy)-N,N,N-trimethylamine

Product 1

HCID 13380183(4-Chlorophenyl)acetic acid tert-butyl esterYield 30.4%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

To a suspension of N,N-dimethyl-formamide-di-tert-butyl acetal (25 ml, 104.4 mmol) in dry toluene (90 ml) was added p-chlorophenyl acetic acid (5.94 g, 34.8 mmol) and the whole heated at 80° C. for 1 h. The mixture was diluted with EtOAc (50 ml) and washed with water (50 ml), 3% aqueous NaHCO3 solution (50 ml) and brine (20 ml) and then dried over MgSO4 and evaporated to give an oil. This oil was purified using 35%, then 50% DCM in pentane to give the title product (2.4 g, 30%); 1HNMR (400 MHz, CDCl3) δ: 1.42 (s, 9H), 3.44 (s, 2H), 7.20 (d, 2H), 7.28 (d, 2H).

Workup

  1. washwashed with water (50 ml), 3% aqueous NaHCO3 solution (50 ml) and brine (20 ml)
  2. dry with materialdried over MgSO4
  3. customevaporated
  4. customto give an oil
  5. customThis oil was purified

Sources & evidence

ORD record
ord-701d47aedcc34c7e947611658d0fc50a
Source dataset
uspto-grants-2005_02
Patent number
US06849649B2

Linked notes

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