Sodium → 5-Fluoro-2,3-dihydrobenzofuran-2-carboxylic acid

HRID 648220Notes

Reaction equation

HRID 648220 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]([C:10]([OH:12])=[O:11])=[CH:7][C:6]=2[CH:13]=1.[Na]>[Na].[Hg].[Hg].[OH-].[Na+]>[F:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][CH:8]([C:10]([OH:12])=[O:11])[CH2:7][C:6]=2[CH:13]=1

Participants

6

Reactant 2

HCID 5360545SodiumHCID 109868725-Fluoro-1-benzofuran-2-carboxylic acid

Product 1

HCID 131024035-Fluoro-2,3-dihydrobenzofuran-2-carboxylic acid

Reagents, catalysts & solvents 3

HCID 23931MercuryCatalystHCID 9837419Sodium amalgamCatalystHCID 14798Sodium HydroxideSolvent

Procedure

5-Fluorobenzofuran-2-carboxylic acid (2.4 g) was added to aqueous sodium hydroxide solution (3.3 g of sodium hydroxide in 50 ml of water). Sodium amalgam was added over 20 minutes (prepared from 1.1 g of sodium and 42 g of mercury). After a further 21/2 hours the solution was left to stand over the amalgam overnight. The mercury was separated and the solution filtered and then treated with excess 4 M sulphuric acid. The precipitated acid was filtered off and dried over P2O5 in vacuo (1.5 g) I.R. νmax 1720 cm-1.

Workup

  1. customThe mercury was separated
  2. filtrationthe solution filtered
  3. additiontreated with excess 4 M sulphuric acid
  4. filtrationThe precipitated acid was filtered off
  5. dry with materialdried over P2O5 in vacuo (1.5 g) I.R

Sources & evidence

ORD record
ord-0640e6b2fddb43a19cd984c8fa702596
Source dataset
uspto-grants-1983_10
Patent number
US04411908

Reaction notes

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