Hydrogen Bromide → HCID 21248920, compound

HRID 1194904Notes

Reaction equation

HRID 1194904 reaction equation
[CH3:1][CH:2]1[CH2:7][CH2:6][CH:5]([C:8](O)([CH3:10])[CH3:9])[CH2:4][CH2:3]1.[BrH:12]>[Br-].[Zn+2].[Br-]>[Br:12][C:8]([CH:5]1[CH2:6][CH2:7][CH:2]([CH3:1])[CH2:3][CH2:4]1)([CH3:10])[CH3:9]

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 10353Dihydro-alpha-terpineol

Product 1

HCID 21248920HCID 21248920, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 10421208Zinc bromideCatalyst

Procedure

2-(4-Methylcyclohexyl)propan-2-ol (0.99 g, 6.39 mmol) was added to a mixture of anhydrous zinc bromide (0.72 g, 3.2 mmol) and 48% HBr (aq). The mixture was stirred at room temperature for 2 h. The mixture was then extracted with diethyl ether (2×20 ml) and the combined extracts were washed with water, dried (MgSO4 /K2CO3) and evaporated under reduced pressure to give the crude title compound as an oil (1.12 g, 80%), νmax (film) 2940, 2915, 2860, 1450, and 1370 cm-1 ; δH (60 MHz, CDCl3) 0.8-2.2 (m), 7.2 (s). Distillation from K2CO3 under reduced pressure removed the impurity resonating at δ7.2.

Workup

  1. extractionThe mixture was then extracted with diethyl ether (2×20 ml)
  2. washthe combined extracts were washed with water
  3. dry with materialdried (MgSO4 /K2CO3)
  4. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-cc4633e3b5794b4992892814466aab5c
Source dataset
uspto-grants-1989_03
Patent number
US04816452

Reaction notes

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