Hydrochloric Acid → 3'-(Hydroxymethyl)-2,3,5,6-tetramethylbiphenyl-4-ol

HRID 453421Notes

Reaction equation

HRID 453421 reaction equation
[OH:1][C:2]1[C:7]([CH3:8])=[C:6]([CH3:9])[C:5]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([CH:16]=[O:17])[CH:11]=2)=[C:4]([CH3:18])[C:3]=1[CH3:19].CO.[BH4-].[Na+].Cl>O1CCCC1>[OH:17][CH2:16][C:12]1[CH:11]=[C:10]([C:5]2[C:4]([CH3:18])=[C:3]([CH3:19])[C:2]([OH:1])=[C:7]([CH3:8])[C:6]=2[CH3:9])[CH:15]=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 4311764Sodium borohydrideHCID 593425904'-Hydroxy-2',3',5',6'-tetramethylbiphenyl-3-carbaldehyde

Product 1

HCID 593426133'-(Hydroxymethyl)-2,3,5,6-tetramethylbiphenyl-4-olYield 93%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 4′-hydroxy-2′,3′,5′,6′-tetramethylbiphenyl-3-carbaldehyde (2.03 g, 8.00 mmol) in a mixed solvent of methanol (10 mL) and tetrahydrofuran (20 mL) was ice-cooled, sodium borohydride (90%, 0.336 g, 8.00 mmol) was added, and the mixture was stirred for 2 hr under nitrogen atmosphere. The reaction mixture was treated with diluted hydrochloric acid, and extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained crystals were recrystallized from heptane-ethyl acetate to give the title compound (1.90 g, yield 93%) as colorless crystals.

Workup

  1. temperaturecooled
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe obtained crystals were recrystallized from heptane-ethyl acetate

Sources & evidence

ORD record
ord-d8f79c94646845f9b50feb47bcddfd7b
Source dataset
uspto-grants-2013_07
Patent number
US08492430B2

Reaction notes

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