3-Chlorophenol → HCID 178521516, compound

HRID 980465Notes

Reaction equation

HRID 980465 reaction equation
[Na].[Cl:2][C:3]1[CH:4]=[C:5]([OH:9])[CH:6]=[CH:7][CH:8]=1.Cl[CH2:11][C:12](=[O:15])[CH2:13][PH4:14]>[Na].CO>[Cl:2][C:3]1[CH:4]=[C:5]([CH:6]=[CH:7][CH:8]=1)[O:9][CH2:11][C:12](=[O:15])[CH2:13][PH4:14]

Participants

5

Reactant 3

HCID 79333-ChlorophenolHCID 5360545SodiumHCID 178521515HCID 178521515, compound

Product 1

HCID 178521516HCID 178521516, compoundYield 177.5%

Reagents, catalysts & solvents 1

HCID 86653488Methanol sodiumSolvent

Procedure

From 5.75 g (0.25 mole) of metallic sodium and 200 ml of methanol sodium methylate is prepared. 32 g (0.25 mole) of m-chloro-phenol are added, the mixture is refluxed for an hour and evaporated to dryness. The solid residue is suspended in 200 ml of benzene and 88 g (0.25 mole) of chloro acetonyl phosphorane are added. The reaction mixture is refluxed for 3 hours. The sodium chloride is removed by filtration of the hot mixture and the benzene filtrate is evaporated in vacuo. The residual solid crude product is rubbed with 50 ml of ether and the crystals formed are filtered and dried. Thus 97 g of the crystalline title compound are obtained, yield 87.2%.

Workup

  1. temperaturethe mixture is refluxed for an hour
  2. customevaporated to dryness
  3. temperatureThe reaction mixture is refluxed for 3 hours
  4. customThe sodium chloride is removed by filtration of the hot mixture
  5. customthe benzene filtrate is evaporated in vacuo
  6. customthe crystals formed
  7. filtrationare filtered
  8. customdried

Sources & evidence

ORD record
ord-0c50f66ce87c414c8e280b35b44020ff
Source dataset
uspto-grants-1987_01
Patent number
US04638002

Reaction notes

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