Hydrochloric Acid → HCID 19363512, compound

HRID 850443Notes

Reaction equation

HRID 850443 reaction equation
[OH-].[Na+].[O-]Cl.[Na+].[OH:6][C:7]1[CH:12]=[CH:11][C:10]([C:13](=[O:16])CBr)=[CH:9][C:8]=1[O:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22].S([O-])([O-])(=[O:25])=S.[Na+].[Na+].Cl>O>[OH:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]([OH:16])=[O:25])=[CH:9][C:8]=1[O:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 24477Sodium ThiosulfateHCID 19363498HCID 19363498, compoundHCID 23665760Sodium Hypochlorite

Product 1

HCID 19363512HCID 19363512, compoundYield 72.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A solution of sodium hydroxide (680 mg), water (21ml) and antiformin (34 ml) was heated to 55° C. 1-(4-Hydroxy-3-pentyloxyphenyl)-2-bromoethanone (3.01 g, 0.01 mol, 1.0 eq) was added, and the mixture was stirred at 60° C.-70° C. for 40 minutes. An aqueous solution (10 ml) of sodium thiosulfate (1.2 g) was added, and the mixture was cooled to room temperature. Conc. hydrochloric acid (5 ml) was added to adjust the mixture to pH 5-6. Water (50 ml) was added to this reaction mixture, and the mixture was extracted twice with ethyl acetate (100 ml). The organic layers were combined, washed with saturated brine (200 ml) and dried over anhydrous sodium sulfate. The drying agent was filtered off, and the filtrate was concentrated under reduced pressure. The obtained residue was purified by column chromatography (n-hexane/ethyl acetate/acetic acid=2/1/0.01) to give 4-hydroxy-3-pentyloxybenzoic acid (1.24 g, 55.3%).

Workup

  1. extractionthe mixture was extracted twice with ethyl acetate (100 ml)
  2. washwashed with saturated brine (200 ml)
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationThe drying agent was filtered off
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customThe obtained residue was purified by column chromatography (n-hexane/ethyl acetate/acetic acid=2/1/0.01)

Sources & evidence

ORD record
ord-69366537f765405f95308aada85a1288
Source dataset
uspto-grants-2000_01
Patent number
US06017919

Reaction notes

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