Hydrochloric Acid → 4-(Phenoxymethyl)benzoic acid

HRID 2120572Notes

Reaction equation

HRID 2120572 reaction equation
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[K+].Cl[CH2:11][C:12]1[CH:20]=[CH:19][C:15]([C:16]([OH:18])=[O:17])=[CH:14][CH:13]=1.Cl>CS(C)=O.C(=O)(O)[O-].[Na+]>[O:7]([CH2:11][C:12]1[CH:20]=[CH:19][C:15]([C:16]([OH:18])=[O:17])=[CH:14][CH:13]=1)[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 996PhenolHCID 14797Potassium HydroxideHCID 742344-(Chloromethyl)benzoic acid

Product 1

HCID 7372674-(Phenoxymethyl)benzoic acidYield 32.4%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 516892Sodium BicarbonateSolvent

Procedure

Phenol 2 (4.706 g, 50.0 mmol) and KOH (6.172 g, 110 mmol) were combined in dimethyl sulfoxide (DMSO) (250 ml). 4-Chloromethylbenzoic acid 1 (8.530 g, 50.0 mmol) was added. The mixture was stirred at room temperature overnight. The mixture was then poured into H20 and acidified with concentrated HCl. The solution was then extracted and concentrated to give a solid. The solid was dissolved in an aqueous sodium bicarbonate solution, then washed with ethyl acetate. The aqueous mixture was then acidified with dilute HCl forming a precipitate which was filtered and dried to give about 3.7 g of 4-phenoxymethylbenzoic acid 3.

Workup

  1. additionThe mixture was then poured into H20
  2. extractionThe solution was then extracted
  3. concentrationconcentrated
  4. customto give a solid
  5. washwashed with ethyl acetate
  6. filtrationwas filtered
  7. customdried

Sources & evidence

ORD record
ord-a00e4d40990b45dabf9ed9e3697dbc33
Source dataset
uspto-grants-2004_02
Patent number
US06693098B2

Reaction notes

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