Hydrochloric Acid → HCID 23039131, compound

HRID 1709019Notes

Reaction equation

HRID 1709019 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 6 M 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 6 M 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-1d353d1b055e411db34afe82118ab18e
Source dataset
uspto-grants-1990_08
Patent number
US04946926

Reaction notes

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