Ethanol → HCID 10590086, compound

HRID 2396259Notes

Reaction equation

HRID 2396259 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].CCO>CCOCC>[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 PBr3 (2.7 g, 10 mmol) in ether (10 mL) was added slowly to a solution of 2,4,6-triisopropylbenzyl alcohol (4.68 g, 20 mmol) in 20 mL of ether at room temperature. The mixture was stirred for 1 hour, 5 mL of absolute EtOH was added, and stirring was continued for another 0.5 hour. The solvent was removed and the residue distributed between EtOAc and saturated Na2CO3. The EtOAc layer was separated, washed with brine, and dried over MgSO4. The solvent was evaporated and the pure product was isolated by column chromatography (100% CH2Cl2, 3.5 g, 59%); NMR (CDCl3): δ 1.2-1.4 (m, 18H), 2.8-3.0(m, 1H), 3.2-3.45 (m, 2H), 4.7 (s, 2H), 7.04 (s, 2H) ppm.

Workup

  1. stirringstirring
  2. waitwas continued for another 0.5 hour
  3. customThe solvent was removed
  4. customThe EtOAc layer was separated
  5. washwashed with brine
  6. dry with materialdried over MgSO4
  7. customThe solvent was evaporated
  8. customthe pure product was isolated by column chromatography (100% CH2Cl2, 3.5 g, 59%)

Sources & evidence

ORD record
ord-cb1b3fb6c9834b9a9e09e6033287c22e
Source dataset
uspto-grants-1996_02
Patent number
US05491172

Reaction notes

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