Hydrochloric Acid → 3,5-Di(hydroxymethyl)phenol

HRID 382853Notes

Reaction equation

HRID 382853 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([C:11](O)=[O:12])[CH:5]=[C:6]([CH:10]=1)[C:7](O)=[O:8].Cl.[OH-].[Na+]>C1COCC1>[OH:12][CH2:11][C:4]1[CH:3]=[C:2]([OH:1])[CH:10]=[C:6]([CH2:7][OH:8])[CH:5]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 692575-Hydroxyisophthalic acid

Product 1

HCID 15194153,5-Di(hydroxymethyl)phenolYield 106.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 5-hydroxyisophthalic acid 1 (30 g, 0.17 mol) in THF (1 L) at room temperature was added slowly a solution of BH3 (800 mL, 1 M in THF). The resulting heterogeneous mixture was warmed to reflux overnight. The reaction mixture was cooled to room temperature whereupon 0.8 L of 1M HCl was carefully added. The resulting homogenous solution was concentrated in vacuo and the residues were treated with NaOH (42 g, 1.05 mol). Water was removed from the solution via concentration in vacuo and the residues were extracted with EtOAc (3×350 mL). The combined organic layers were dried (MgSO4), filtered and concentrated in vacuo to give 28 g (93%) of triol 2 as thick colorless oil.

Workup

  1. temperatureThe resulting heterogeneous mixture was warmed
  2. temperatureto reflux overnight
  3. additionwas carefully added
  4. concentrationThe resulting homogenous solution was concentrated in vacuo
  5. customWater was removed from the solution via concentration in vacuo
  6. extractionthe residues were extracted with EtOAc (3×350 mL)
  7. dry with materialThe combined organic layers were dried (MgSO4)
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-618cd7609a854e5f94d8a5b4a0c227db
Source dataset
uspto-grants-2001_10
Patent number
US06310244B1

Reaction notes

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