Acetic Acid → HCID 13066701, compound

HRID 1163980Notes

Reaction equation

HRID 1163980 reaction equation
[N+](=C)=[N-].[OH:4][C:5]1[CH:21]=[CH:20][CH:19]=[CH:18][C:6]=1[O:7][C:8]1[C:16]2[O:15][C:14](=[O:17])[CH2:13][C:12]=2[CH:11]=[CH:10][CH:9]=1.[C:22](O)(=O)C>C(OCC)C.O1CCOCC1>[CH3:22][O:4][C:5]1[CH:21]=[CH:20][CH:19]=[CH:18][C:6]=1[O:7][C:8]1[C:16]2[O:15][C:14](=[O:17])[CH2:13][C:12]=2[CH:11]=[CH:10][CH:9]=1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 9550DiazomethaneHCID 13066700HCID 13066700, compound

Product 1

HCID 13066701HCID 13066701, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent2×HCID 312751,4-DioxaneSolvent

Procedure

An excess of a solution of diazomethane in diethyl ether was added to a solution of 7-(2-hydroxyphenoxy)2,3-dihydrobenzofuran-2-one (4.9 g) in a mixture of diethyl ether (50 ml) and dioxane (50 ml), and allowed to stand overnight at room temperature. To the reaction mixture was added acetic acid (1 ml), and the organic solvent was distilled off. The oily residue was purified by column chromatography, and the crude crystals were crystallized from ethyl acetate to give 7-(2-methoxyphenoxy)-2,3-dihydrobenzofuran-2-one (2.3 g). mp 171°-172° C.

Workup

  1. distillationthe organic solvent was distilled off
  2. customThe oily residue was purified by column chromatography
  3. customthe crude crystals were crystallized from ethyl acetate

Sources & evidence

ORD record
ord-67d9943046cf477fb977525623241b55
Source dataset
uspto-grants-1983_01
Patent number
US04367238

Reaction notes

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