Hydrochloric Acid → HCID 86736360, compound

HRID 1391158Notes

Reaction equation

HRID 1391158 reaction equation
[C:1]([CH:4]([CH2:17][CH2:18][CH2:19][CH:20]([OH:26])[CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[CH2:5][CH2:6][CH2:7][C:8]1[CH:16]=[CH:15][C:11](C(O)=O)=[CH:10][CH:9]=1)(=[O:3])[CH3:2].[OH-].[Na+].[BH4-].[Na+].Cl.OC(C(CCCC(O)CCCCC)CCCC1C=CC([C:43]([OH:45])=[O:44])=CC=1)C>O.CCOCC>[OH:3][CH:1]([CH:4]([CH2:17][CH2:18][CH2:19][CH:20]([OH:26])[CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[CH2:5][CH2:6][CH2:7][C:8]1[CH:9]=[CH:10][CH:11]=[CH:15][C:16]=1[C:43]([OH:45])=[O:44])[CH3:2]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 4311764Sodium borohydrideHCID 20386034HCID 20386034, compoundHCID 203860504-(4-Acetyl-8-hydroxytridecyl)benzoic acid

Product 1

HCID 86736360HCID 86736360, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

4-(4-Acetyl-8-hydroxytridecyl)benzoic acid (7.2 g., 0.02 mole) is dissolved in a solution of sodium hydroxide (1.2 g., 0.03 mole) in water (80 ml.). Sodium borohydride (0.76 g., 0.02 mole) is added and the resulting solution is let stand at 25°-27° C. for 21 hours. The mixture is then acidified to Congo Red with concentrated hydrochloric acid. The thick oil which separates is taken up in ether, washed with water, and dried over magnesium sulfate. The ether is evaporated and the crude product chromatographed on a column containing 100 g. of silica gel. Elution with 4% methanol in chloroform affords 4.9 g. (68%) of pure 4-[4-(1-hydroxyethyl)-8-hydroxytridecyl]benzoic acid as a colorless viscous oil which gradually partially solidifies to a wax.

Workup

  1. customat 25°-27° C.
  2. customfor 21 hours
  3. washwashed with water
  4. dry with materialdried over magnesium sulfate
  5. customThe ether is evaporated
  6. customthe crude product chromatographed on a column
  7. additioncontaining 100 g
  8. washElution with 4% methanol in chloroform
  9. customaffords 4.9 g

Sources & evidence

ORD record
ord-19cd0dea67c6499687d80a5c2725264e
Source dataset
uspto-grants-1979_02
Patent number
US04140861

Reaction notes

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