Hydrochloric Acid → HCID 14850669, compound

HRID 727841Notes

Reaction equation

HRID 727841 reaction equation
[CH:1]([C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[CH:5][CH:4]=1)=[O:2].[CH2:12]([Mg]Br)[CH2:13][CH3:14].Cl>O1CCCC1>[OH:2][CH:1]([C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[CH:5][CH:4]=1)[CH2:12][CH2:13][CH3:14]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 120884-Formylbenzoic acidHCID 178455851HCID 178455851, compound

Product 1

HCID 14850669HCID 14850669, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

6 g of 4-formylbenzoic acid is dissolved in 100 ml of tetrahydrofuran and mixed with 100 ml of a 1-molar solution of propyl magnesium bromide in tetrahydrofuran. After 6 hours of reaction time at room temperature the mixture is stirred into 100 ml of 2M of hydrochloric acid, extracted with ether and the ether phase is concentrated by evaporation. The crystalline material is filtered off with toluene on a suction filter and dissolved in 45 ml of dioxane and 5 ml of water and treated with 1.5 g of sodium boron hydride. After 15 minutes at room temperature, the mixture is added to 1M of hydrochloric acid, extracted with ethyl acetate, dried, concentrated by evaporation and chromatographed on 120 g of silica gel [toluene/acetic acid/water (10:10:1); upper phase after addition of a little water)]. 4.04 g of 4-(1-hydroxybutyl)-benzoic acid with a melting point of 109°-113° C. is obtained.

Workup

  1. customAfter 6 hours of reaction time at room temperature the mixture
  2. extractionextracted with ether
  3. concentrationthe ether phase is concentrated by evaporation
  4. filtrationThe crystalline material is filtered off with toluene on a suction
  5. filtrationfilter
  6. dissolutiondissolved in 45 ml of dioxane
  7. addition5 ml of water and treated with 1.5 g of sodium boron hydride
  8. additionthe mixture is added to 1M of hydrochloric acid
  9. extractionextracted with ethyl acetate
  10. customdried
  11. concentrationconcentrated by evaporation
  12. customchromatographed on 120 g of silica gel [toluene/acetic acid/water (10:10:1)
  13. additionupper phase after addition of a little water)]

Sources & evidence

ORD record
ord-4f27f03ffaf847b19ad60ab132314852
Source dataset
uspto-grants-1991_09
Patent number
US05045558

Reaction notes

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