Hydrochloric Acid → 4-(3,3,4,4,4-Pentafluorobutyl)benzenemethanol

HRID 630314Notes

Reaction equation

HRID 630314 reaction equation
C([O:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][CH2:13][C:14]([F:20])([F:19])[C:15]([F:18])([F:17])[F:16])=[CH:8][CH:7]=1)(=O)C.[OH-].[K+].Cl>CO>[F:19][C:14]([F:20])([C:15]([F:16])([F:17])[F:18])[CH2:13][CH2:12][C:9]1[CH:8]=[CH:7][C:6]([CH2:5][OH:4])=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 874686924-(3,3,4,4,4-Pentafluorobutyl)benzenemethanol acetate

Product 1

HCID 866134414-(3,3,4,4,4-Pentafluorobutyl)benzenemethanolYield 87%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

4-(3,3,4,4,4-Pentafluorobutyl)benzenemethanol acetate (525 mg, 1.42 mmol) was heated to reflux with aqueous potassium hydroxide solution (40%; 399 μL, 2.84 mmol) in methanol (6 mL) for two hours. The residue was acidified with 1 M aqueous hydrochloric acid, and extracted with ethyl acetate. The combined organic layers were concentrated under reduced pressure. Flash chromatography gave 314 mg of 4-(3,3,4,4,4-pentafluorobutyl)benzenemethanol; 1H NMR (300 MHz, CDCl3) δ 7.33 (d, 2H), 7.21 (d, 2H), 4.68 (dbr, 2H), 2.91 (m, 2H), 2.32 (m, 2H), 1.71 (tbr, 1H) ppm.

Workup

  1. extractionextracted with ethyl acetate
  2. concentrationThe combined organic layers were concentrated under reduced pressure

Sources & evidence

ORD record
ord-dbe1127b28514f659a5914e27b92b0fb
Source dataset
uspto-grants-2016_04
Patent number
US09315509B2

Reaction notes

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