Acetic Acid → 5-(3-Methylundecan-2-yl)benzene-1,3-diol

HRID 1579558Notes

Reaction equation

HRID 1579558 reaction equation
C[O:2][C:3]1[CH:10]=[C:9]([CH:11]([CH3:22])[CH:12]([CH3:21])[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])[CH:8]=[C:5]([O:6]C)[CH:4]=1.C(O)(=O)C.Br>O>[CH3:22][CH:11]([C:9]1[CH:10]=[C:3]([OH:2])[CH:4]=[C:5]([CH:8]=1)[OH:6])[CH:12]([CH3:21])[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 260Hydrogen BromideHCID 68139039HCID 68139039, compound

Product 1

HCID 215687715-(3-Methylundecan-2-yl)benzene-1,3-diol

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 30.6 g. of 5-(1,2-dimethyldecyl)-resorcinol dimethyl ether in 350 ml. of glacial acetic acid and 150 ml. of 48% hydrogen bromide is refluxed eight hours, then stirred at 25° for 12 hours. The reaction mixture is diluted with water and extracted three times with ether. The combined extracts are washed with saturated aqueous sodium bisulfite and saturated aqueous sodium bicarbonate, dried (MgSO4), concentrated and distilled to give 5-(1,2-dimethyldecyl)resorcinol.

Workup

  1. extractionextracted three times with ether
  2. washThe combined extracts are washed with saturated aqueous sodium bisulfite and saturated aqueous sodium bicarbonate
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. distillationdistilled

Sources & evidence

ORD record
ord-d66ca460bb184823af2805c4ac128ba7
Source dataset
uspto-grants-1976_01
Patent number
US03931232

Reaction notes

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