Acetic Acid → HCID 13298049, compound

HRID 2396131Notes

Reaction equation

HRID 2396131 reaction equation
[C:1]1([C:7]2([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH:11]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[CH2:10][CH2:9]O2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br.C(=O)([O-])[O-].[Na+].[Na+].[C:31]([OH:34])(=[O:33])[CH3:32]>>[C:31]([O:34][CH2:9][CH2:10][C:11]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[C:7]([C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)(=[O:33])[CH3:32]

Participants

5

Reactant 4

HCID 176Acetic Acid2×HCID 260Hydrogen BromideHCID 10340Sodium CarbonateHCID 13298048HCID 13298048, compound

Product 1

HCID 13298049HCID 13298049, compound

Conditions

Temperature
75 °C

Procedure

30.0 g of 2,2,3-triphenyltetrahydrofuran are dissolved in 125 ml of acetic acid, after which 25 ml of 40% hydrogen-bromide in acetic acid are added. The mixture is stirred for 1 h at 75° C. The solvent is evaporated,and 1M sodium carbonate solution is added in excess. The product is extracted in toluene. The toluene solution is dried over sodium sulfate and the solvent is evaporated. The product is recrystallized from aqueous methanol and then has m.p 81-3° C. The yield is 28.7 g (84%).

Workup

  1. additionis added in excess
  2. extractionThe product is extracted in toluene
  3. dry with materialThe toluene solution is dried over sodium sulfate
  4. customthe solvent is evaporated
  5. customThe product is recrystallized from aqueous methanol
  6. customhas m.p 81-3° C

Sources & evidence

ORD record
ord-67d4b860b42644f1ade1b0601ae27a40
Source dataset
uspto-grants-1996_02
Patent number
US05491173

Reaction notes

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