Phenol → [(1R,5S)-5-Hydroxycyclopent-2-en-1-yl]acetic acid

HRID 918259Notes

Reaction equation

HRID 918259 reaction equation
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:8]([O-])([O-:13])([O:10]CC)C>>[OH:7][C@H:1]1[CH2:6][CH:5]=[CH:4][C@H:3]1[CH2:2][C:8]([OH:13])=[O:10]

Participants

3

Reactant 2

HCID 996PhenolHCID 86598186Ethyl ortho-acetate

Product 1

HCID 12813247[(1R,5S)-5-Hydroxycyclopent-2-en-1-yl]acetic acid

Procedure

In the same manner as described in Example 1 but using 0.5 part of phenol in place of the hydroquinone, 7 parts of unreacted ethyl orthoacetate was recovered and then 4.2 parts of the desired product, a lactone of cis-2-hydroxy-cyclopent-4-ene-1-acetic acid was obtained.

Workup

  1. customwas recovered

Sources & evidence

ORD record
ord-36670f1655184ab0bbbbec30f7e23d1f
Source dataset
uspto-grants-1976_07
Patent number
US03970673

Reaction notes

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