Hydrochloric Acid → HCID 67894087, compound
Reaction equation
[CH2:1]([O:13][C:14]1[CH:19]=[CH:18][C:17]([CH2:20][C:21]([O:23][CH2:24][C:25]([O:27]CC)=O)=[O:22])=[CH:16][CH:15]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].CC(C)([O-])C.[K+].Cl>C1COCC1.CN(C=O)C>[CH2:1]([O:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]2[C:21]([O:23][CH2:24][C:25]=2[OH:27])=[O:22])=[CH:16][CH:15]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]Participants
Procedure
In a mixture of THF (50 ml) and DMF (10 ml) was dissolved ethoxycarbonylmethyl 4-dodecyloxyphenylacetate (5.0 g, 0.013 mol.). To the solution was added at room temperature potassium tertiary butoxide (2 g, 0.017 mol.). The mixture was stirred at room temperature for one hour, after which was added 2N HCl (20 ml). The resultant mixture was extracted with ethyl acetate. The organic layer was washed with water, dried and concentrated under reduced pressure The resultant crude crystals were recrystallized from IPE-ethyl acetate to give 2-(4-dodecyloxyphenyl)-3-hydroxy-2-buten-4-olide (4-h, 3.0 g, 70%). By a procedure analogous to the above, compounds (4-a to 4-c, 4-f, 4-j to 4-m) were synthesized. Physico-chemical properties and NMR spectra of these compounds are shown in Table 7.
Workup
- extractionThe resultant mixture was extracted with ethyl acetate
- washThe organic layer was washed with water
- customdried
- concentrationconcentrated under reduced pressure The resultant crude crystals
- customwere recrystallized from IPE-ethyl acetate
Sources & evidence
- ORD record
- ord-6a45c01a8c934030a27a16c09c018529
- Source dataset
- uspto-grants-1990_07
- Patent number
- US04939274
Reaction notes
Loading…