Hydrogen Bromide → Phenol, 4-hexadecyl-

HRID 1950690Notes

Reaction equation

HRID 1950690 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])=[CH:5][CH:4]=1.Br.C1(C)C=CC=CC=1>[Br-].C([P+](CCCC)(CCCC)CCCCCCCCCCCCCCCC)CCC.O>[CH2:9]([C:6]1[CH:5]=[CH:4][C:3]([OH:2])=[CH:8][CH:7]=1)[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24]

Participants

6

Reactant 3

HCID 260Hydrogen BromideHCID 1140TolueneHCID 141439341-Hexadecyl-4-methoxybenzene

Product 1

HCID 75768Phenol, 4-hexadecyl-

Reagents, catalysts & solvents 2

HCID 84716Hexadecyltributylphosphonium bromideCatalystHCID 962WaterSolvent

Conditions

Temperature
135 °C

Procedure

The alkyl anisole of Example 1 (40 g) was transferred to a dry 3-neck 1-litre flask under nitrogen. To this was added tributylhexadecylphosphonium bromide (12.69 g) and HBr (48% aq., 71.4 ml). The resulting thick suspension was warmed to 135° C. and stirred for five hours. Toluene was added and the reaction was transferred to a separating funnel. The organic layer was shaken with water and then the aqueous extract shaken with fresh toluene. The organic extracts were combined and dried with MgSO4. The solvent was removed in vacuo to give the title compound as a brown solid.

Workup

  1. customthe reaction was transferred to a separating funnel
  2. extractionthe aqueous extract
  3. stirringshaken with fresh toluene
  4. dry with materialdried with MgSO4
  5. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-561e088031d9415eabe5d14cf3b3d33b
Source dataset
uspto-grants-2013_03
Patent number
US08404627B2

Reaction notes

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