5-Benzyloxy-alpha,alpha,alpha',alpha'tetramethyl-1,3-benzenedimethanol → 3,5-Bis(1-methylethyl)phenol

HRID 393404

Reaction equation

C([O:8][C:9]1[CH:10]=[C:11]([C:19]([CH3:22])([CH3:21])O)[CH:12]=[C:13]([C:15]([CH3:18])([CH3:17])O)[CH:14]=1)C1C=CC=CC=1>C(O)C.Cl.[C].[Pd]>[CH:15]([C:13]1[CH:14]=[C:9]([OH:8])[CH:10]=[C:11]([CH:19]([CH3:22])[CH3:21])[CH:12]=1)([CH3:18])[CH3:17]

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of 5-benzyloxy-α,α,α′,α′-tetramethyl-1,3-benzenedimethanol (22.9 g, 76 mmol) in ethanol (500 mL), concentrated hydrochloric acid (2.6 mL) and a 10% palladium-carbon catalyst (8.0 g) were added. Under hydrogen atmosphere, the mixture was stirred for 23 hours at 60° C. The reaction mixture was subjected to filtration, and the filtrate was concentrated under reduced pressure, to thereby yield 13.6 g of 3,5-diisopropylphenol as a solid (yield 100%). The solid was crystallized from hexane, to thereby yield colorless needles.

Workup

filtrationThe reaction mixture was subjected to filtration
concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record: ord-8d6cd646ce274afb8122d80d40d75890
Source dataset: uspto-grants-2004_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06806395B2

Linked notes

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