2-[2-Hydroxy-3-(2-chlorophenoxy)phenyl]butyric acid → 3-Ethyl-7-(2-chlorophenoxy)-2,3-dihydrobenzofuran-2-one

HRID 1164049Notes

Reaction equation

HRID 1164049 reaction equation
CO[C:3]1[C:8]([O:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[Cl:16])=[CH:7][CH:6]=[CH:5][C:4]=1[CH:17]([CH2:21][CH3:22])[C:18]([OH:20])=[O:19].OC1C(OC2C=CC=CC=2Cl)=CC=CC=1C(CC)C(O)=O>C(OC(=O)C)(=O)C.I>[CH2:21]([CH:17]1[C:4]2[CH:5]=[CH:6][CH:7]=[C:8]([O:9][C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[Cl:16])[C:3]=2[O:19][C:18]1=[O:20])[CH3:22]

Participants

5

Reactant 2

HCID 205134172-[2-Hydroxy-3-(2-chlorophenoxy)phenyl]butyric acidHCID 205134672-[2-Methoxy-3-(2-chlorophenoxy)phenyl]butyric acid

Product 1

HCID 130667113-Ethyl-7-(2-chlorophenoxy)-2,3-dihydrobenzofuran-2-oneYield 62.3%

Reagents, catalysts & solvents 2

HCID 7918Acetic AnhydrideSolvent2×HCID 24841Hydrogen iodideSolvent

Procedure

A solution of 2-[2-methoxy-3-(2-chlorophenoxy)phenyl]butyric acid (4.1 g) in acetic anhydride (10 ml) and hydriodic acid (55-58%, 20 ml) were treated in a similar manner to that of Example 10-(7). The resultant oily residue, i.e. 2-[2-hydroxy-3-(2-chlorophenoxy)phenyl]butyric acid was treated with acetic anhydride (10 ml) in a similar manner to that of Example 10-(7). The resultant crystalline residue was recrystallized from ethanol to give 3-ethyl-7-(2-chlorophenoxy)-2,3-dihydrobenzofuran-2-one (2.3 g). mp 78°-79° C.

Workup

  1. customThe resultant crystalline residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-c7f839cfc352414c8dd4e167226ba344
Source dataset
uspto-grants-1983_01
Patent number
US04367238

Reaction notes

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