Water → HCID 54402081, compound

HRID 259207Notes

Reaction equation

HRID 259207 reaction equation
[OH:1][C:2]([CH3:28])([CH2:23][CH2:24][O:25][CH2:26][CH3:27])[CH:3]=[CH:4][CH:5]1[CH2:13][CH2:12][C:7]2(OCC[O:8]2)[CH:6]1[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][C:20]([OH:22])=[O:21].O>C(O)(=O)C>[OH:1][C:2]([CH3:28])([CH2:23][CH2:24][O:25][CH2:26][CH3:27])[CH:3]=[CH:4][CH:5]1[CH:6]([CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][C:20]([OH:22])=[O:21])[C:7](=[O:8])[CH2:12][CH2:13]1

Participants

4

Reactant 2

HCID 962WaterHCID 54456189HCID 54456189, compound

Product 1

HCID 54402081HCID 54402081, compoundYield 106.5%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Crude 7-{7-(3-hydroxy-3-methyl-5-ethoxypent-1-enyl)-1,4-dioxaspiro[4,4]non-6-yl}heptanoic acid (0.38 g.), water (8 ml.) and glacial acetic acid (16 ml.) were left to stand at room temperature for 6 hours. The solution was then evaporated in vacuo at a temperature lower than 50° C. Ethyl acetate (150 ml.) was added, and then the solution washed with water (until the pH of the washings was pH 5), dried over sodium sulphate, and evaporated to give 7-[5-(3-hydroxy-3-methyl-5-ethoxypent-1-enyl)-2-oxocyclopentyl]heptanoic acid (0.36 g.), νmax 980 cm-1, 1700 cm-1, 1730 cm-1.

Workup

  1. customThe solution was then evaporated in vacuo at a temperature lower than 50° C
  2. additionEthyl acetate (150 ml.) was added
  3. washthe solution washed with water (until the pH of the washings
  4. dry with materialdried over sodium sulphate
  5. customevaporated

Sources & evidence

ORD record
ord-b8c8dee53fee4676bcfcf57bbbf35d9c
Source dataset
uspto-grants-1977_07
Patent number
US04036872

Reaction notes

Loading…