4-[1,1,1,3,3,3-hexafluoro-2-(methoxymethyl)oxypropan-2-yl]-2-[(1Z)-1-propenyl]-6-propylphenol → HCID 59234895, compound

HRID 1919759Notes

Reaction equation

HRID 1919759 reaction equation
[F:1][C:2]([F:26])([F:25])[C:3]([C:12]1[CH:17]=[C:16]([CH2:18][CH2:19][CH3:20])[C:15]([OH:21])=[C:14](/[CH:22]=[CH:23]\[CH3:24])[CH:13]=1)([O:8][CH2:9][O:10][CH3:11])[C:4]([F:7])([F:6])[F:5]>[C].[Pd].CO>[CH2:18]([C:16]1[CH:17]=[C:12]([C:3]([O:8][CH2:9][O:10][CH3:11])([C:2]([F:1])([F:25])[F:26])[C:4]([F:5])([F:6])[F:7])[CH:13]=[C:14]([CH2:22][CH2:23][CH3:24])[C:15]=1[OH:21])[CH2:19][CH3:20]

Participants

4

Reactant 1

HCID 592350754-[1,1,1,3,3,3-hexafluoro-2-(methoxymethyl)oxypropan-2-yl]-2-[(1Z)-1-propenyl]-6-propylphenol

Product 1

HCID 59234895HCID 59234895, compoundYield 72%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

Methanol (30 mL) was added to 4-[1,1,1,3,3,3-hexafluoro-2-(methoxymethyl)oxypropan-2-yl]-2-[(1Z)-1-propenyl]-6-propylphenol (1.29 g, 3.34 mmol). A 10% palladium-carbon catalyst (130 mg) was added to the mixed solution, followed by hydrogenation for 20 hours. The catalyst was separated from the reaction solution by filtration, followed by concentration under reduced pressure to obtain 929 mg of 2,6-dipropyl-4-[1,1,1,3,3,3-hexafluoro-2-(methoxymethyl)oxypropan-2-yl]phenol (yield: 72%) as white crystals.

Workup

  1. customThe catalyst was separated from the reaction solution by filtration
  2. concentrationfollowed by concentration under reduced pressure

Sources & evidence

ORD record
ord-db2b022b96954f16a41f9f3bd120968a
Source dataset
uspto-grants-2012_05
Patent number
US08168666B2

Reaction notes

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