Methyl 3-(2-(tert-butoxy)-2-oxoethoxy)benzoate → [3-(Methoxycarbonyl)phenoxy]acetic acid

HRID 1843690Notes

Reaction equation

HRID 1843690 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]([CH:17]=[CH:18][CH:19]=1)[O:8][CH2:9][C:10]([O:12]C(C)(C)C)=[O:11])=[O:4]>FC(F)(F)C(O)=O.C1(OC)C=CC=CC=1.ClCCl>[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]([CH:17]=[CH:18][CH:19]=1)[O:8][CH2:9][C:10]([OH:12])=[O:11])=[O:4]

Participants

5

Reactant 1

HCID 16094634Methyl 3-(2-(tert-butoxy)-2-oxoethoxy)benzoate

Product 1

HCID 13816150[3-(Methoxycarbonyl)phenoxy]acetic acidYield 86%

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolventHCID 7519AnisoleSolvent

Procedure

A solution of t-butyl [3-(methoxycarbonyl)phenoxy]acetate in trifluoroacetic acid (1 kg), anisole (100 mL) and dichloromethane (1 L) was stirred at room temperature for 48 hours. The reaction mixture was concentrated and then the residue was crystallized from diisopropyl ether to obtain the title compound (467 g, 86%) as a white solid.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customthe residue was crystallized from diisopropyl ether

Sources & evidence

ORD record
ord-b38f9c98b5864a879d1efd653c9006d9
Source dataset
uspto-grants-2015_02
Patent number
US08946264B2

Reaction notes

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