Hydrochloric Acid → 2-Chloro-4-(1-hydroxyoctadecyl)benzoic acid

HRID 1381720Notes

Reaction equation

HRID 1381720 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]([C:11](=[O:29])[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[BH4-].[Na+].O.Cl>C(O)C>[Cl:1][C:2]1[CH:10]=[C:9]([CH:11]([OH:29])[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 4311764Sodium borohydride3×HCID 15592211HCID 15592211, compound

Product 1

HCID 565572-Chloro-4-(1-hydroxyoctadecyl)benzoic acidYield 93.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent3×

Procedure

To 159 mg of product from Example 11 suspended in 10 ml of ethyl alcohol at 0° C. was added 13 mg of sodium borohydride. An additional 10 ml of ethyl alcohol was added and the reaction stirred overnight while allowed to warm to room temperature. An additional 40 mg of sodium borohydride was added followed in about 20 hours by 50 ml of ethanol and 100 mg of sodium borohydride. Stirring was continued for 20 hours whereupon 25 ml of water was added, followed by 20 ml of 10% hydrochloric acid. The organic solvent was removed using a rotary evaporator and the aqueous residue extracted with two 50 ml portions of ethyl ether. The organic extracts were combined, washed with water, dried over sodium sulfate, and filtered. The solvent was removed using a rotary evaporator to give a white solid (150 mg). Recrystallization of the solid from methanol/hexane gave 139 mg of product identical with that disclosed in Example 14 of U.S. Pat. No. 4,469,885.

Workup

  1. stirringStirring
  2. additionwas added
  3. customThe organic solvent was removed
  4. customa rotary evaporator
  5. extractionthe aqueous residue extracted with two 50 ml portions of ethyl ether
  6. washwashed with water
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. customThe solvent was removed
  10. customa rotary evaporator

Sources & evidence

ORD record
ord-24cabdea76cc4411b44ffe99919285d1
Source dataset
uspto-grants-1989_02
Patent number
US04803294

Reaction notes

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