Hydrochloric Acid → HCID 23039131, compound

HRID 2166460Notes

Reaction equation

HRID 2166460 reaction equation
[OH:1][C:2]1[CH:17]=[CH:16][C:5]([O:6][C:7]2[CH:8]=[C:9]([CH:13]=[CH:14][CH:15]=2)[C:10]([OH:12])=[O:11])=[CH:4][CH:3]=1.[OH-].[Na+].[C:20](OC(=O)C)(=[O:22])[CH3:21].Cl>>[C:20]([O:1][C:2]1[CH:17]=[CH:16][C:5]([O:6][C:7]2[CH:8]=[C:9]([CH:13]=[CH:14][CH:15]=2)[C:10]([OH:12])=[O:11])=[CH:4][CH:3]=1)(=[O:22])[CH3:21]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 7918Acetic AnhydrideHCID 14798Sodium HydroxideHCID 1618523-(4-Hydroxyphenoxy)benzoic acid

Product 1

HCID 23039131HCID 23039131, compoundYield 85.1%

Conditions

Temperature
0 °C

Procedure

An amount of 3-(4'-hydroxyphenoxy)benzoic acid (9.772 g, 42.45 millimoles (mmoles)) was dissolved in 6M NaOH (18 ml, 108 mmoles) and cooled in an ice bath. Acetic anhydride (8.0 ml, 11.1 g, 109 mmoles) was added cautiously to the basic solution at such a rate as to maintain 0° to 5° C. and then stirred vigorously for an additional 15 minutes (min) at 0° C. The reaction mixture was then allowed to warm to room temperature over 1 hour. The aqueous solution was acidified with 6M HCl (18 ml, 108 mmoles) and extracted with 75 ml of ethyl acetate. The organic solution was washed three times with a 50 ml saturated solution of NaCl, dried with MgSO4, filtered, and solvent evaporated. The crude product was taken up in methanol, treated with activated carbon, filtered through a celite pad, and evaporated. Recrystallization of the product gave 9.83 g of 3-(4'-acetoxyphenoxy)benzoic acid as an off-white powder with a m.p. 141° C. to 143° C.

Workup

  1. temperaturecooled in an ice bath
  2. temperatureto maintain 0° to 5° C.
  3. temperatureto warm to room temperature over 1 hour
  4. extractionextracted with 75 ml of ethyl acetate
  5. washThe organic solution was washed three times with a 50 ml saturated solution of NaCl
  6. dry with materialdried with MgSO4
  7. filtrationfiltered
  8. customsolvent evaporated
  9. additiontreated with activated carbon
  10. filtrationfiltered through a celite pad
  11. customevaporated
  12. customRecrystallization of the product

Sources & evidence

ORD record
ord-6f399105b0d54e39883afc2d2b0c305a
Source dataset
uspto-grants-1990_07
Patent number
US04945150

Reaction notes

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