2,6-Di-tert-butyl-4-(chloromethyl)phenol → (3,5-Di-tert-butyl-4-hydroxy-benzyl)-cyclohexyl-phosphinic acid methyl ester

HRID 1661847

Reaction equation

HRID 1661847 reaction equation
C[O:2][P:3]([CH:6]1[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1)[O:4][CH3:5].[C:12]([C:16]1[CH:17]=[C:18]([CH:21]=[C:22]([C:25]([CH3:28])([CH3:27])[CH3:26])[C:23]=1[OH:24])[CH2:19]Cl)([CH3:15])([CH3:14])[CH3:13]>C1(C)C=CC=CC=1>[CH3:5][O:4][P:3]([CH2:19][C:18]1[CH:17]=[C:16]([C:12]([CH3:13])([CH3:15])[CH3:14])[C:23]([OH:24])=[C:22]([C:25]([CH3:28])([CH3:27])[CH3:26])[CH:21]=1)([CH:6]1[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1)=[O:2]

Participants

4

Reactant 2

HCID 123786012,6-Di-tert-butyl-4-(chloromethyl)phenolHCID 21678155Dimethylcyclohexylphosphonite

Product 1

HCID 57909097(3,5-Di-tert-butyl-4-hydroxy-benzyl)-cyclohexyl-phosphinic acid methyl esterYield 51.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 10.47 grams (59 mmol) of dimethylcyclohexylphosphonite with 15.14 grams (59 mmol) of 3,5-di-tert-butyl-4-hydroxybenzyl chloride (CAS REG # 955-01-1) in 45 mL of toluene is refluxed for 2 hours and is cooled. The resultant precipitated crystals are collected by filtration, washed with toluene, then hexane and are dried under vacuum to obtain 11.5 grams (51% yield) of (3,5-di-tert-butyl-4-hydroxy-benzyl)-cyclohexyl-phosphinic acid methyl ester as a white solid mp 149-150° C.

Workup

  1. temperatureis refluxed for 2 hours
  2. temperatureis cooled
  3. customThe resultant precipitated crystals
  4. filtrationare collected by filtration
  5. washwashed with toluene
  6. dry with materialhexane and are dried under vacuum

Sources & evidence

ORD record
ord-e40d7e2e6f504d5cb0f0acf81a2d09f5
Source dataset
uspto-grants-2011_10
Patent number
US08030435B2

Linked notes

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