Phosphoric Acid → 4-Hydroxy-4-methyl-5-(prop-2-en-1-yl)cyclopent-2-en-1-one

HRID 1073695Notes

Reaction equation

HRID 1073695 reaction equation
[CH3:1][C:2]1[O:11][C:5]([CH:6](O)[CH2:7][CH:8]=[CH2:9])=[CH:4][CH:3]=1.P([O-])([O-])(O)=[O:13].[K+].[K+].P(=O)(O)(O)O>O>[CH2:7]([CH:6]1[C:2]([OH:11])([CH3:1])[CH:3]=[CH:4][C:5]1=[O:13])[CH:8]=[CH2:9]

Participants

5

Reactant 3

HCID 1004Phosphoric AcidHCID 24450Potassium Phosphate, DibasicHCID 110625572-(1-hydroxy-3-butenyl)-5-methyl furan

Product 1

HCID 128798724-Hydroxy-4-methyl-5-(prop-2-en-1-yl)cyclopent-2-en-1-oneYield 80%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

In the same apparatus as in Example 1, 5-methyl-allyl-furfuryl alcohol (50 parts) and a buffer solution prepared from water (1500 parts) and dipotassium monohydrogen phosphate (1.7 parts) and adjusted to pH 5.1 with phosphoric acid were charged, and the resultant mixture was stirred at 100° C. in a nitrogen stream until the starting compound was consumed. The reaction mixture was treated as in Example 1 to give 2-allyl-3-hydroxy-3-methyl-4-cyclopentenone in a yield of 80 %.

Workup

  1. additionwere charged
  2. customwas consumed
  3. additionThe reaction mixture was treated as in Example 1

Sources & evidence

ORD record
ord-627baeafa549496b8524eb7a461d6c84
Source dataset
uspto-grants-1990_11
Patent number
US04970345

Reaction notes

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