Sodium Hydroxide → HCID 59606751, compound

HRID 1627927Notes

Reaction equation

HRID 1627927 reaction equation
C(N(CC)C(=O)[O:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([Cl:12])[C:7]=1[CH2:13][CH2:14][CH2:15][OH:16])C.[OH-].[Na+]>C(O)C>[Cl:12][C:8]1[C:7]([CH2:13][CH2:14][CH2:15][OH:16])=[C:6]([OH:5])[CH:11]=[CH:10][CH:9]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 59606761HCID 59606761, compound

Product 1

HCID 59606751HCID 59606751, compoundYield 213.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of the 3-chloro-2-(3-hydroxypropyl)phenyl diethylcarbamate (0.410 g; 1.43 mmol) in ethanol (14.5 ml) was added solid sodium hydroxide (0.144 g; 3.59 mmol) and the reaction mixture was heated at reflux for 21 h. After cooling, the volatiles were removed under reduced pressure, water was added and the mixture was extracted with diethyl ether, the combined organics were dried over magnesium sulphate, filtered and concentrated under reduced pressure. Purification by flash chromatography on silica gel using a gradient of ethyl acetate (15-100%) in heptane furnished 0.57 g (79%) of the desired 3-chloro-2-(3-hydroxypropyl)phenol.

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureat reflux for 21 h
  3. temperatureAfter cooling
  4. customthe volatiles were removed under reduced pressure, water
  5. additionwas added
  6. extractionthe mixture was extracted with diethyl ether
  7. dry with materialthe combined organics were dried over magnesium sulphate
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customPurification by flash chromatography on silica gel using a gradient of ethyl acetate (15-100%) in heptane

Sources & evidence

ORD record
ord-f77bb94f068d4459bb906d426aed348c
Source dataset
uspto-grants-2014_07
Patent number
US08785638B2

Reaction notes

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