Trifluoroacetic acid → 2-[2-(2-Methylphenyl)ethoxy]acetic acid

HRID 1741457Notes

Reaction equation

HRID 1741457 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][CH2:9][OH:10].C([O:15][C:16](=[O:19])[CH2:17]Br)(C)(C)C.[OH-].[Na+].FC(F)(F)C(O)=O>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.ClCCl.C1(C)C=CC=CC=1>[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][CH2:9][O:10][CH2:17][C:16]([OH:19])=[O:15]

Participants

8

Reactant 4

HCID 6422Trifluoroacetic acidHCID 14798Sodium HydroxideHCID 79177tert-Butyl bromoacetateHCID 882672-Methylphenethyl alcohol

Product 1

HCID 187790542-[2-(2-Methylphenyl)ethoxy]acetic acid

Reagents, catalysts & solvents 3

HCID 74236Tetrabutylammonium BromideCatalystHCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Procedure

The subtitle compound (8.91 g) was prepared according to the procedure in example 5 part a using 2-(2-methylphenyl)ethanol (5.0 g), t-butylbromoacetate (5.47 ml), tetrabutylammoniumbromide (0.78 g), toluene (80 ml), 50% aqueous sodium hydroxide (40 ml), trifluoroacetic acid (20 ml) and dichloromethane (20 ml).

Sources & evidence

ORD record
ord-53894f1308584277b022d6bb35502eb8
Source dataset
uspto-grants-1999_10
Patent number
US05973167

Reaction notes

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