Sodium Hydroxide → HCID 21387541, compound

HRID 1833853Notes

Reaction equation

HRID 1833853 reaction equation
[BH4-].[Na+].[Cl:3][C:4]1[CH:16]=[CH:15][CH:14]=[CH:13][C:5]=1[C:6]([C:8]1[O:9][CH:10]=[CH:11][CH:12]=1)=[O:7].[OH-].[Na+]>CO.O>[Cl:3][C:4]1[CH:16]=[CH:15][CH:14]=[CH:13][C:5]=1[CH:6]([C:8]1[O:9][CH:10]=[CH:11][CH:12]=1)[OH:7]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 4311764Sodium borohydrideHCID 21387596(2-Chlorophenyl)(furan-2-yl)methanone

Product 1

HCID 21387541HCID 21387541, compoundYield 70.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Portions of sodium borohydride (total 15 g.) were added over an hour to a stirred solution of 2-(2-chlorobenzoyl)furan (prepared as hereinbefore described; 100 g.) in methanol (500 ml.) at 10°-25° C. After stirring for 1 hour, the solution was heated briefly to the boiling point and, when effervescence had ceased, sodium hydroxide solution (2N, 100 ml.) was added. The solution was heated at reflux for 30 minutes, diluted with water (1 liter) and extracted with diethyl ether (4 × 150 ml.). The combined extracts were washed with water (2 × 100 ml.), dried over sodium sulphate, filtered and evaporated to a clear oil, which was distilled to give (±) 2-(2-chloro-α-hydroxybenzyl)furan (71 g.), b.p. 136° C./0.1 mm.Hg, as a viscous yellow oil.

Workup

  1. temperaturethe solution was heated briefly to the boiling point and, when effervescence
  2. temperatureThe solution was heated
  3. temperatureat reflux for 30 minutes
  4. extractionextracted with diethyl ether (4 × 150 ml.)
  5. washThe combined extracts were washed with water (2 × 100 ml.)
  6. dry with materialdried over sodium sulphate
  7. filtrationfiltered
  8. customevaporated to a clear oil, which
  9. distillationwas distilled

Sources & evidence

ORD record
ord-0d5304bca913410ca35ccfe53ed52d6d
Source dataset
uspto-grants-1978_01
Patent number
US04067723

Reaction notes

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