Water → {3-[2-(2-Chloroacetamido)-2-methylpropyl]phenyl}acetic acid

HRID 1866515Notes

Reaction equation

HRID 1866515 reaction equation
S(=O)(=O)(O)O.O[C:7]([CH3:20])([CH3:19])[CH2:8][C:9]1[CH:10]=[C:11]([CH2:15][C:16]([OH:18])=[O:17])[CH:12]=[CH:13][CH:14]=1.[Cl:21][CH2:22][C:23]#[N:24].[OH2:25]>C(O)(=O)C>[Cl:21][CH2:22][C:23]([NH:24][C:7]([CH3:20])([CH3:19])[CH2:8][C:9]1[CH:10]=[C:11]([CH2:15][C:16]([OH:18])=[O:17])[CH:12]=[CH:13][CH:14]=1)=[O:25]

Participants

6

Reactant 4

HCID 962WaterHCID 1118Sulfuric AcidHCID 7856ChloroacetonitrileHCID 46938719[3-(2-Hydroxy-2-methylpropyl)phenyl]acetic acid

Product 1

HCID 46938812{3-[2-(2-Chloroacetamido)-2-methylpropyl]phenyl}acetic acid

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Concentrated sulphuric acid (21 ml) was added dropwise to a solution of [3-(2-hydroxy-2-methylpropyl)-phenyl]-acetic acid (Preparation 49) (10.6 g, 51.0 mmol) and chloroacetonitrile (4.8 ml, 76.0 mmol) in glacial acetic acid (16 ml) at 0° C. The reaction was allowed to warm to room temperature and after 2 hours was poured onto iced water (500 ml). The aqueous was extracted with ethyl acetate (2×250 ml) and the combined organics washed with brine (50 ml), dried (sodium sulfate), and the solvent removed in vacuo to furnish the title compound as a golden oil (14.0 g). 1H NMR (400 MHz, CDCl3): δ=7.31-7.06 (4H, m), 6.19 (1H, bs), 3.95 (2H, s), 3.62 (2H, s), 3.02 (2H, s), 1.36 (6H, s) ppm. LRMS (electrospray): m/z [M−H]− 282/284.

Workup

  1. extractionThe aqueous was extracted with ethyl acetate (2×250 ml)
  2. washthe combined organics washed with brine (50 ml)
  3. dry with materialdried (sodium sulfate)
  4. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-46c5326685aa431ca1f7f549a00b30d1
Source dataset
uspto-grants-2009_12
Patent number
US07629358B2

Reaction notes

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