Hydrochloric Acid → Tetradecanoic acid, 2-[4-[(butylsulfonyl)amino]phenoxy]-

HRID 1703450Notes

Reaction equation

HRID 1703450 reaction equation
C([O:3][C:4](=[O:33])[CH:5]([O:18][C:19]1[CH:24]=[CH:23][C:22]([NH:25][S:26]([CH2:29][CH2:30][CH2:31][CH3:32])(=[O:28])=[O:27])=[CH:21][CH:20]=1)[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])C.C(O)C.[OH-].[Na+].Cl>O>[CH2:29]([S:26]([NH:25][C:22]1[CH:23]=[CH:24][C:19]([O:18][CH:5]([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])[C:4]([OH:33])=[O:3])=[CH:20][CH:21]=1)(=[O:28])=[O:27])[CH2:30][CH2:31][CH3:32]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 14798Sodium HydroxideHCID 53822991HCID 53822991, compound2×

Product 1

HCID 112696Tetradecanoic acid, 2-[4-[(butylsulfonyl)amino]phenoxy]-

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

92 g (0.19 mol) of ethyl-α-[p-butylsulfonylaminophenoxy]tetradecanoate (Intermediate II) obtained in Step B, and 500 ml of ethyl alcohol were placed in a 3-necked flask. A solution of 20 g of sodium hydroxide (dissolved in a minimum amount of water) was added with good stirring. The reaction mixture was refluxed for 3 hours, allowed to cool to room temperature, poured into ice water and acidified with concentrated hydrochloric acid. The oil was extracted with ether, washed with water and saturated sodium chloride solution. The ether was removed under vacuo to give a gummy solid. After trituration with ligroine (boiling point: 35°-60° C.), the solid was collected. Yield was 50 g of Intermediate III, m.p. 80°-82° C. TLC analysis (benzene) showed one product.

Workup

  1. customwere placed in a 3-necked flask
  2. additionwas added with good stirring
  3. temperatureThe reaction mixture was refluxed for 3 hours
  4. extractionThe oil was extracted with ether
  5. washwashed with water and saturated sodium chloride solution
  6. customThe ether was removed under vacuo
  7. customto give a gummy solid
  8. customAfter trituration with ligroine (boiling point: 35°-60° C.), the solid was collected

Sources & evidence

ORD record
ord-40d01c78d0944e7d99fb1b3faf4808cd
Source dataset
uspto-grants-1978_11
Patent number
US04124396

Reaction notes

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