Phosphoric Acid → 4-Hydroxy-2-(3-benzyloxybenzyl)cyclopent-2-enone

HRID 1803633Notes

Reaction equation

HRID 1803633 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH:6](O)[CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:9]=1.[OH:23]P([O-])(O)=O.[K+].[OH:29]P(O)(O)=O.[Na+].[Cl-]>O>[OH:23][CH:3]1[CH2:4][C:5](=[O:1])[C:6]([CH2:7][C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([O:14][CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH:9]=2)=[CH:2]1.[OH:29][CH:2]1[CH:6]([CH2:7][C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([O:14][CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH:9]=2)[C:5](=[O:1])[CH:4]=[CH:3]1

Participants

7

Reactant 4

HCID 1004Phosphoric AcidHCID 5234Sodium ChlorideHCID 516951Monobasic potassium phosphateHCID 71170040HCID 71170040, compound

Product 2

HCID 711700344-Hydroxy-2-(3-benzyloxybenzyl)cyclopent-2-enoneHCID 711700374-Hydroxy-5-(3-benzyloxybenzyl)cyclopent-2-enone

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
120 °C

Procedure

1-(Furan-2-yl)-2-(3-benzyloxyphenyl)ethan-1-ol (3.97 kg, 13.49 mol) and KH2PO4 (120 g, 0.88 mol) was added to H2O (120 L) and H3PO4 was added until pH=3. The reaction was kept being stirred at 120° C. for 5 hours. After being cooled, NaCl (25 kg) was added, and the reaction was extracted with EtOAc, dried over MgSO4, and evaporated to give the crude 4-hydroxy-2-(3-benzyloxybenzyl)cyclopent-2-enone and 4-hydroxy-5-(3-benzyloxybenzyl)cyclopent-2-enone as black oil: 3.4 kg (crude yield: 85%).

Workup

  1. additionwas added until pH=3
  2. temperatureAfter being cooled
  3. extractionthe reaction was extracted with EtOAc
  4. dry with materialdried over MgSO4
  5. customevaporated

Sources & evidence

ORD record
ord-42203a1653da4d6ca6fa4e22ac191d05
Source dataset
uspto-grants-2013_01
Patent number
US08350090B1

Reaction notes

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