Hydrogen Bromide → HCID 69111032, compound

HRID 2214325Notes

Reaction equation

HRID 2214325 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C@H:10]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH3:11])=[CH:5][CH:4]=1.Br>C(O)(=O)C>[OH:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:9][C@H:10]([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH3:11])=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 69111235HCID 69111235, compound

Product 1

HCID 69111032HCID 69111032, compoundYield 99.5%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Into a 1 L four-necked flask equipped with a condenser tube, 28.55 g of (R)-(−)-1-(4-methoxyphenyl)-2-phenylpropane, 570 mL of acetic acid and 59 mL of 48% hydrobromic acid were charged, and a reaction was carried out at 110° C. for 7 hours. After cooling, acetic acid was distilled off under reduced pressure, and 100 mL of water and 140 mL of toluene were added thereto. The organic phase was separated, the aqueous phase was extracted with toluene, the toluene layer and the organic phase were put together, the solvent was distilled off under reduced pressure, and the obtained crystals were recrystallized from methanol to obtain 26.65 g of (R)-(−)-1-(4-hydroxyphenyl)-2-phenylpropane [H-Ph-CH(CH3)—CH2-Ph-OH] (yield: 99.5%).

Workup

  1. customInto a 1 L four-necked flask equipped with a condenser tube
  2. temperatureAfter cooling
  3. distillationacetic acid was distilled off under reduced pressure, and 100 mL of water and 140 mL of toluene
  4. additionwere added
  5. customThe organic phase was separated
  6. extractionthe aqueous phase was extracted with toluene
  7. distillationthe solvent was distilled off under reduced pressure
  8. customthe obtained crystals were recrystallized from methanol

Sources & evidence

ORD record
ord-2cfbae88bd884263a851024f2e7eae31
Source dataset
uspto-grants-2006_09
Patent number
US07108895B2

Reaction notes

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