Sulfuric Acid → 4-Bromo-2-(1-methylcyclohexyl)phenol

HRID 1681569Notes

Reaction equation

HRID 1681569 reaction equation
C(O[C:5](=O)[CH3:6])(=O)C.S(=O)(=O)(O)O.[Br:13][C:14]1[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=1>>[Br:13][C:14]1[CH:19]=[CH:18][C:17]([OH:20])=[C:16]([C:5]2([CH3:6])[CH2:18][CH2:19][CH2:14][CH2:15][CH2:16]2)[CH:15]=1

Participants

4

Reactant 3

HCID 1118Sulfuric AcidHCID 78084-BromophenolHCID 7918Acetic Anhydride

Product 1

HCID 105638754-Bromo-2-(1-methylcyclohexyl)phenolYield 66.6%

Procedure

There are then slowly added 10.8 ml (117 mmoles) of acetic anhydride and the reaction mixture is stirred at ambient temperature for 18 hours. 2.7 ml (50 mmoles) of concentrated sulfuric acid are then added and in small portions 17.3 g (100 mmoles) of 4-bromophenol. The reaction mixture is stirred at ambient temperature for 24 hours, evaporated to dryness and taken up in 200 ml of water. The pH is adjusted to 7 with sodium bicarbonate and extracted with ethylether. The organic phase is decanted, dried over magnesium sulfate and evaporated. The residue is purified by chromatography on a silica column by using as the eluant a 40/60 mixture of dichloromethane and hexane. The solvents are evaporated and 8.97 g (33% yield) of 4-bromo-2-(1-methylcyclohexyl) phenol in the form of a yellowish oil are obtained.

Workup

  1. customevaporated to dryness
  2. extractionextracted with ethylether
  3. customThe organic phase is decanted
  4. dry with materialdried over magnesium sulfate
  5. customevaporated
  6. customThe residue is purified by chromatography on a silica column
  7. additiona 40/60 mixture of dichloromethane and hexane
  8. customThe solvents are evaporated

Sources & evidence

ORD record
ord-cf4980c769e44e71b79dcae9e078c4f3
Source dataset
uspto-grants-1992_12
Patent number
US05173289

Reaction notes

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