Water → HCID 66768907, compound

HRID 590640

Reaction equation

HRID 590640 reaction equation
[CH2:1]=[CH:2][CH2:3]/[CH:4]=[CH:5]\[CH2:6]/[CH:7]=[CH:8]\[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]1[CH:21]=[C:20](O)[CH:19]=[CH:18][CH:17]=1.[Al+3].[Cl-].[Cl-].[Cl-].[C:27](Cl)([CH3:30])([CH3:29])[CH3:28].[OH2:32]>>[C:27]([CH:14]([CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])[CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[OH:32])([CH3:30])([CH3:29])[CH3:28]

Participants

5

Reactant 4

HCID 962WaterHCID 10486tert-BUTYL CHLORIDEHCID 6451240Aluminum(III) ChlorideHCID 11266523Cardanol

Product 1

HCID 66768907HCID 66768907, compound

Procedure

2-Tert-butyl pentadecylphenol is prepared as disclosed in Fuel, 82 (2003), the disclosure of which is totally incorporated herein by reference. More specifically, hydrogenated cardanol (0.84 mol) is added to a three-neck round bottom flask containing AlCl3 (0.15 mol) and the system is cooled to a temperature between 0 and 5° C. Tert-butyl chloride (0.25 mol) is then slowly added from a dropping funnel with constant stirring over 4 hours. The formation of the product is monitored by thin layer chromatography (TLC). Thereafter, crushed ice and water are added to the mixture to allow thorough decomposition of intermediate compounds. Separation of two distinct phases is observed, one of the phases turning into a very viscous dark oil. After phase separation, the mixture is distilled under reduced pressure and the product collected and dried with anhydrous Na2SO4. The product is then purified through a silica gel chromatographic column using solutions of CHCl3 and n-hexane of several compositions from 0 to 100% as eluents to yield a compound of the formula

Workup

  1. temperaturethe system is cooled to a temperature between 0 and 5° C
  2. additionare added to the mixture
  3. customSeparation of two distinct phases
  4. customAfter phase separation
  5. distillationthe mixture is distilled under reduced pressure
  6. customthe product collected
  7. dry with materialdried with anhydrous Na2SO4
  8. customThe product is then purified through a silica gel chromatographic column
  9. customto yield a compound of the formula

Sources & evidence

ORD record
ord-8edb79a32011426c9e47cbc8c460760c
Source dataset
uspto-grants-2016_01
Patent number
US09234109B2

Linked notes

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