2,2'-(5-Hydroxy-1,3-phenylene)bis(propan-2-ol) → 3,5-Bis(1-methylethyl)phenol

HRID 393405

Reaction equation

HRID 393405 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([C:12]([CH3:15])([CH3:14])O)[CH:5]=[C:6]([C:8]([CH3:11])([CH3:10])O)[CH:7]=1>C(O)C.Cl.[C].[Pd]>[CH:8]([C:6]1[CH:7]=[C:2]([OH:1])[CH:3]=[C:4]([CH:12]([CH3:15])[CH3:14])[CH:5]=1)([CH3:11])[CH3:10]

Participants

5

Reactant 1

HCID 226603332,2'-(5-Hydroxy-1,3-phenylene)bis(propan-2-ol)

Product 1

HCID 931043,5-Bis(1-methylethyl)phenolYield 97.3%

Reagents, catalysts & solvents 3

HCID 178418390HCID 178418390, compoundCatalystHCID 313Hydrochloric AcidSolventHCID 702EthanolSolvent

Procedure

To a solution of 5-hydroxy-α,α,α′,α′-tetramethyl-1,3-benzenedimethanol (20.0 g, 95.1 mmol) in ethanol (600 mL), concentrated hydrochloric acid (12.0 mL) and a 10% palladium-carbon catalyst (11.0 g) were added, and the mixture was stirred under hydrogen atmosphere for 22 hours at room temperature. The reaction mixture was subjected to filtration, and the filtrate was concentrated under reduced pressure, to thereby yield a white solid. The thus-obtained solid was crystallized from hexane, to thereby yield 16.5 g of 3,5-diisopropylphenol as colorless needles (yield 97.3%).

Workup

  1. filtrationThe reaction mixture was subjected to filtration
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customto thereby yield a white solid
  4. customThe thus-obtained solid was crystallized from hexane

Sources & evidence

ORD record
ord-72d8ee25c369452891b9524d80abc868
Source dataset
uspto-grants-2004_10
Patent number
US06806395B2

Linked notes

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