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

HRID 2090067Notes

Reaction equation

HRID 2090067 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=[O:10])=[CH:4][CH:3]=1>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][C:9]([O:11][C:5]([CH3:8])([CH3:6])[CH3:4])=[O:10])=[CH:6][CH:7]=1

Participants

3

Reactant 1

HCID 15880(4-Chlorophenyl)acetic acid

Product 1

HCID 13380183(4-Chlorophenyl)acetic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-chlorophenylacetic acid (10.0 g, 58.6 mmol) in CH2Cl2 was added 2-Cert-butyl-1,3-diisopropyl-isourea (50 g, 250 mmol) dropwise at −10° C. The mixture was stirred at room temperature overnight, then the precipitate was, removed by filtration. The filtrate was washed with 1M HCl (aq) and saturated NaCl (aq), dried over Na2SO4, filtered, and concentrated. The residue was purified by silica gel chromatography eluting with 2% EtOAc/petroleum ether to afford the title compound: 1H NMR (CD3OD, 300 MHz) δ 7.26-7.30 (m, 2H), 7.18-7.21 (m, 2H), 3.49 (s, 2H), 1.43 (s, 9H).

Workup

  1. customremoved by filtration
  2. washThe filtrate was washed with 1M HCl (aq) and saturated NaCl (aq)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel chromatography
  7. washeluting with 2% EtOAc/petroleum ether

Sources & evidence

ORD record
ord-8999f10ede194e26843892e53f6dc10e
Source dataset
uspto-grants-2013_05
Patent number
US08436015B2

Reaction notes

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