Acetyl chloride → methyl 7-(6-oxocyclohex-1-enyl)hept-5Z-enoate

HRID 1706036Notes

Reaction equation

HRID 1706036 reaction equation
[O:1]=[C:2]1[CH:7]([CH2:8]/[CH:9]=[CH:10]\[CH2:11][CH2:12][CH2:13][C:14]([OH:16])=[O:15])[CH:6]=[CH:5][CH2:4][CH2:3]1.[C:17](Cl)(=O)C>CO>[O:1]=[C:2]1[C:7]([CH2:8]/[CH:9]=[CH:10]\[CH2:11][CH2:12][CH2:13][C:14]([O:16][CH3:17])=[O:15])=[CH:6][CH2:5][CH2:4][CH2:3]1

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 705947957-(6-oxocyclohex-2enyl)hept-5Z-enoic acid

Product 1

HCID 70598135methyl 7-(6-oxocyclohex-1-enyl)hept-5Z-enoate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 13.0 g of crude 7-(6-oxocyclohex-2-enyl)-hept-5Z-enoic acid in 200 ml of dry methanol was stirred under argon as 2 ml of acetyl chloride was added. The resultant yellow solution was left to stand for 2.6 days (on another occasion 16 hours was found to be sufficient). Solvent was removed by evaporation in vacuo and the residue was dissolved in ether and washed with saturated aqueous sodium bicarbonate. The wash solution was back extracted with ether. The combined ether extracts were dried (MgSO4) and evaporated in vacuo to yield 11.6 g of crude methyl 7-(6-oxocyclohex-1-enyl)hept-5Z-enoate as a yellow oil. This product was purified by chromatography on silicic acid-Celite (85:15) using benzene to ethyl acetate gradient elution to give 0.78 g of ca. 80% pure material and 8.41 g of pure material: ir (film) 9.17, 8.55, 8.33, 8.00, 7.30, 7.04, 5.95, 5.74, and 3.39μ; nmr δ 1.3-2.5 (m, 12H), 2.9 (m, 2H), 3.67 (s, 3H), 5.45 (m,2H) and 6.7 (m,1H).

Workup

  1. additionwas added
  2. waitThe resultant yellow solution was left
  3. customon another occasion 16 hours
  4. customSolvent was removed by evaporation in vacuo
  5. dissolutionthe residue was dissolved in ether
  6. washwashed with saturated aqueous sodium bicarbonate
  7. extractionThe wash solution was back extracted with ether
  8. dry with materialThe combined ether extracts were dried (MgSO4)
  9. customevaporated in vacuo

Sources & evidence

ORD record
ord-6fdf14acef7e4c6e8db11a5fd7299dbc
Source dataset
uspto-grants-1980_06
Patent number
US04206127

Reaction notes

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