Acetic Acid → HCID 86735635, compound

HRID 262905Notes

Reaction equation

HRID 262905 reaction equation
[C:1]([CH2:4][CH2:5][CH2:6][CH2:7]/[CH:8]=[CH:9]\[C:10]1[C:11](=[O:16])[CH2:12][CH:13](O)[CH:14]=1)([OH:3])=[O:2].[SH:17][CH2:18][CH2:19][OH:20].C[O-].[Na+].C(O)(=O)C>CO>[C:1]([CH2:4][CH2:5][CH2:6][CH2:7]/[CH:8]=[CH:9]\[C:10]1[C:11](=[O:16])[CH2:12][CH:13]([S:17][CH2:18][CH2:19][OH:20])[CH:14]=1)([OH:3])=[O:2]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 15672-MercaptoethanolHCID 10942334Sodium MethoxideHCID 86732967HCID 86732967, compound

Product 1

HCID 86735635HCID 86735635, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a stirred solution of 2.24 g. (10 mmols) of 2-(6-carboxy-2-cis-hexenyl)-4-hydroxycyclopent-2-en-1-one (U.S. Pat. No. 3,952,033) and 0.82 g (10.5 mmols) of β-mercaptoethanol in 50 ml of methanol is added 10.5 ml of N/1 sodium methoxide in methanol solution during 30 minutes at room temperature. After the addition the solution is stirred at room temperature for 1 hour and treated with 4.8 g of glacial acetic acid (80 mmols). The solution is concentrated to volume of 10 ml, treated with 30 ml of brine, and extracted with ethyl acetate. The extract is washed with brine, dried over magnesium sulfate, and concentrated.

Workup

  1. additionAfter the addition the solution
  2. concentrationThe solution is concentrated to volume of 10 ml
  3. additiontreated with 30 ml of brine
  4. extractionextracted with ethyl acetate
  5. washThe extract is washed with brine
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-bf0d1da90b994e249f6c651bb46e269f
Source dataset
uspto-grants-1979_05
Patent number
US04154954

Reaction notes

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