HCID 54220051, compound → HCID 14348594, compound

HRID 980759Notes

Reaction equation

HRID 980759 reaction equation
[CH:1]([C:6]1[C:11]([CH3:12])=[C:10]([O:13][CH3:14])[C:9]([CH3:15])=[CH:8][C:7]=1[CH2:16][CH2:17][CH2:18][C:19]([O:21]C)=[O:20])=[CH:2][C:3](=[O:5])[CH3:4].C(OC)(=O)[CH2:24][C:25](OC)=[O:26].[Na]>CO>[C:19]([CH2:18][CH2:17][CH2:16][C:7]1[C:6]([CH:1]2[CH2:24][C:25](=[O:26])[CH:4]=[C:3]([OH:5])[CH2:2]2)=[C:11]([CH3:12])[C:10]([O:13][CH3:14])=[C:9]([CH3:15])[CH:8]=1)([OH:21])=[O:20]

Participants

4

Reactant 2

HCID 54220051HCID 54220051, compoundHCID 86741238HCID 86741238, compound

Product 1

HCID 14348594HCID 14348594, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

Methyl 4-(2-(but-1-en-3-one-1-yl)-3,5-dimethyl-4-methoxyphenyl)butyrate (5.0 g) and sodium dimethyl malonate (6 g equiv) were stirred and heated at reflux in dry methanol (60 ml) for 6 hr. The solvent was evaporated under reduced pressure and the residue was heated at reflux with a 10% excess of an aqueous potassium hydroxide solution (60 ml) for 8 hr. The cooled mixture was extracted with diethyl ether. The aqueous fraction was heated to 60° C. and was acidified by slow addition of a dilute aqueous hydrochloric acid solution. The cooled mixture was extracted with ethyl acetate. The dried (MgSO4) organic fraction was evaporated to give 5-(6-[3-(carboxy)propyl]-2,4-dimethyl-3-methoxyphenyl)-3-hydroxycyclohex-2-en-1-one as a pale yellow foam. Pmr spectrum (acetone-d6 ; δ in ppm): 1.6-3.7 (11H,m); 2.28 (3H,m); 2.43 (3H,s); 3.65 (3H,s); 5.52 (1H,s); 6.91 (1H,s); 8.6 (2H,brs).

Workup

  1. temperatureheated
  2. customThe solvent was evaporated under reduced pressure
  3. temperaturethe residue was heated
  4. temperatureat reflux with a 10% excess of an aqueous potassium hydroxide solution (60 ml) for 8 hr
  5. extractionThe cooled mixture was extracted with diethyl ether
  6. additionwas acidified by slow addition of a dilute aqueous hydrochloric acid solution
  7. extractionThe cooled mixture was extracted with ethyl acetate
  8. dry with materialThe dried (MgSO4) organic fraction
  9. customwas evaporated

Sources & evidence

ORD record
ord-74f6112ddb5a463e92b2f83847e4ddb6
Source dataset
uspto-grants-1987_01
Patent number
US04639267

Reaction notes

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