Benzyl Chloride → HCID 21544470, compound

HRID 1606754Notes

Reaction equation

HRID 1606754 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:10]=1)[C:5]([OH:7])=[O:6].[H-].[Na+].[CH2:17](Cl)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>CS(C)=O>[CH2:17]([O:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([C:11]([F:12])([F:13])[F:14])[CH:10]=1)[C:5]([OH:7])=[O:6])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 7503Benzyl ChlorideHCID 24758Sodium hydrideHCID 27831463-hydroxy-5-(trifluoromethyl)benzoic Acid

Product 1

HCID 21544470HCID 21544470, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution resulting from 206 mg. (1 m mole) of 3-hydroxy-5-trifluoromethylbenzoic acid* and 85 mg. (2 m moles) of a 56.6% oil suspension of sodium hydride in 2 ml. of dimethylsulfoxide is added 127 mg. (1 m mole) of benzyl chloride and the reaction mixture heated to 90° C. for 1-2 hours. The mixture is cooled to room temperature, diluted with 10 ml. of water and extracted with ether. The aqueous phase is separated and acidified with 6N hydrochloric acid. The precipitated produce is filtered, dried and sublimed at 125° C. and .05 mm pressure, m.p. 143°-145° C.

Workup

  1. customTo a solution resulting from 206 mg
  2. additiondiluted with 10 ml
  3. extractionof water and extracted with ether
  4. customThe aqueous phase is separated
  5. customThe precipitated produce
  6. filtrationis filtered
  7. customdried
  8. customsublimed at 125° C.

Sources & evidence

ORD record
ord-32cd656fcf37441eaca01d8d67bf68ab
Source dataset
uspto-grants-1976_04
Patent number
US03953595

Reaction notes

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