Potassium nitrite → 2-(2,3-Dihydrobenzofuran-5-yl)-2-hydroxyacetic acid

HRID 1390211Notes

Reaction equation

HRID 1390211 reaction equation
[H][H].N[CH:4]([C:8]1[CH:9]=[CH:10][C:11]2[O:15][CH2:14][CH2:13][C:12]=2[CH:16]=1)[C:5]([OH:7])=[O:6].N([O-])=[O:18].[Na+].N([O-])=O.[K+]>C(O)(=O)C>[OH:18][CH:4]([C:8]1[CH:9]=[CH:10][C:11]2[O:15][CH2:14][CH2:13][C:12]=2[CH:16]=1)[C:5]([OH:7])=[O:6]

Participants

6

Reactant 4

HCID 516910Potassium nitriteHCID 205312232-Amino-2-(2,3-dihydro-1-benzofuran-5-yl)acetic acidHCID 23668193Sodium NitriteHCID 178418361HCID 178418361, compound

Product 1

HCID 233358212-(2,3-Dihydrobenzofuran-5-yl)-2-hydroxyacetic acid

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

The compound of formula 3 wherein W is a hydroxyl group may be prepared from the corresponding amine compound of formula 3, W is --NHR3 and R3 is hydrogen. One equivalent of α-amino(2,3-dihydro-5-benzofuranyl)acetic acid in a suitable acid such as hydrochloric, hydrobromic, sulfuric, phosphoric or acetic acid is reacted with 1 to 3 equivalents of an alkali metal nitrite such as sodium nitrite or potassium nitrite at a temperature of from 30° to 70° C. for from 2 to 8 hours to give the desired α-hydroxy(2,3-dihydro-5-benzofuranyl)acetic acid.

Sources & evidence

ORD record
ord-ecb53c28497941eb99ad8347e35c37d5
Source dataset
uspto-grants-1979_02
Patent number
US04138397

Reaction notes

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