2-Hydroxybenzonitrile → HCID 20378968, compound

HRID 2083267Notes

Reaction equation

HRID 2083267 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[OH:9])#[N:2].[Na].[C:11]([O:15][CH2:16][CH:17]([OH:30])[CH2:18]OS(C1C=CC(C)=CC=1)(=O)=O)([CH3:14])([CH3:13])[CH3:12].[OH-].[Na+]>COCCO.O>[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[O:9][CH2:18][CH:17]([OH:30])[CH2:16][O:15][C:11]([CH3:14])([CH3:13])[CH3:12])#[N:2]

Participants

7

Reactant 4

HCID 119072-HydroxybenzonitrileHCID 14798Sodium HydroxideHCID 5360545SodiumHCID 20378967HCID 20378967, compound

Product 1

HCID 20378968HCID 20378968, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 80192-MethoxyethanolSolvent2×

Procedure

o-Cyanophenol (5.95 g.) is added to a solution of sodium (1.15 g.) in 2-methoxyethanol (20 ml.), the mixture is stirred for 5 minutes, and a solution of 3-t-butoxy-1-toluene-p-sulphonyloxypropan-2-ol (15.1 g.) in 2-methoxyethanol (30 ml.) is added. The mixture is heated under reflux for 90 minutes, cooled and poured into a mixture of ice and water (150 ml.) and the mixture is basified with aqueous 2N-sodium hydroxide solution and extracted twice with chloroform (100 ml. each time). The combined extracts are washed with water, dried and evaporated to dryness and the residue is chromatographed on a silica gel column using chloroform as eluant. The appropriate fractions of the eluate are evaporated to dryness and there is thus obtained as oily residue 1-o-cyanophenoxy-3-t-butoxypropan-2-ol, the structure of which is confirmed by proton magnetic resonance spectroscopy.

Workup

  1. temperatureThe mixture is heated
  2. temperatureunder reflux for 90 minutes
  3. temperaturecooled
  4. extractionextracted twice with chloroform (100 ml
  5. washThe combined extracts are washed with water
  6. customdried
  7. customevaporated to dryness
  8. customthe residue is chromatographed on a silica gel column
  9. customThe appropriate fractions of the eluate are evaporated to dryness and there

Sources & evidence

ORD record
ord-dcdd3db50cb34fb29775da1f63253330
Source dataset
uspto-grants-1978_04
Patent number
US04085136

Reaction notes

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