Ethanol → HCID 10590086, compound

HRID 850279Notes

Reaction equation

HRID 850279 reaction equation
P(Br)(Br)[Br:2].[CH:5]([C:8]1[CH:15]=[C:14]([CH:16]([CH3:18])[CH3:17])[CH:13]=[C:12]([CH:19]([CH3:21])[CH3:20])[C:9]=1[CH2:10]O)([CH3:7])[CH3:6].C(O)C>C(OCC)C>[CH:5]([C:8]1[CH:15]=[C:14]([CH:16]([CH3:18])[CH3:17])[CH:13]=[C:12]([CH:19]([CH3:21])[CH3:20])[C:9]=1[CH2:10][Br:2])([CH3:7])[CH3:6]

Participants

5

Reactant 3

HCID 702EthanolHCID 24614Phosphorus tribromideHCID 10728422HCID 10728422, compound

Product 1

HCID 10590086HCID 10590086, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of phosphorus tribromide (3.8 mL, 0.04 mol) in ethyl ether (150 mL) was added dropwise to 2,4,6-triisopropylbenzyl alcohol (17.99 g, 0.076 mol) in ethyl ether (350 mL) at room temperature under a nitrogen atmosphere. The reaction mixture was stirred overnight at room temperature. Ethanol (95%, 50 mL) was added dropwise over 1 hour and the resulting mixture was stirred for 30 minutes, and was then concentrated to an oil. The oil was partitioned between ethyl acetate (300 mL) and saturated aqueous sodium bicarbonate. The organic layer was washed with water (50 mL), dried (magnesium sulfate), filtered, and concentrated to a clear liquid (22.56 g, 98.9%). This was used directly in the next step.

Workup

  1. stirringthe resulting mixture was stirred for 30 minutes
  2. concentrationwas then concentrated to an oil
  3. customThe oil was partitioned between ethyl acetate (300 mL) and saturated aqueous sodium bicarbonate
  4. washThe organic layer was washed with water (50 mL)
  5. dry with materialdried (magnesium sulfate)
  6. filtrationfiltered
  7. concentrationconcentrated to a clear liquid (22.56 g, 98.9%)

Sources & evidence

ORD record
ord-523bb32aba7a4117b9b8950b6c66088f
Source dataset
uspto-grants-2000_01
Patent number
US06017905

Reaction notes

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