Hydrochloric Acid → HCID 178458878, compound

HRID 703368Notes

Reaction equation

[C:1]([C:5]1[C:6](=[O:31])[CH2:7][CH:8]([C:17]2[CH:22]=[CH:21][C:20]([O:23][CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)=[CH:19][CH:18]=2)[CH:9](C(OCC)=O)[C:10]=1[OH:11])(=[O:4])[CH2:2][CH3:3].[OH-].[Na+].Cl>C(O)C.O>[C:1]([C:5]1[C:6](=[O:31])[CH2:7][CH:8]([C:17]2[CH:22]=[CH:21][C:20]([O:23][CH2:24][C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=3)=[CH:19][CH:18]=2)[CH2:9][C:10]=1[OH:11])(=[O:4])[CH2:2][CH3:3]

Participants

Conditions

Temperature: 70 °C

Procedure

A mixture of 54 g (0.13 mol) of 2-propionyl-3-hydroxy-5-(4-benzyloxyphenyl)-4-(carboethoxy)cyclohex-2-en-1-one and 30 g (0.37 mol) of 50 percent sodium hydroxide in 450 mL of 95 percent ethanol and 100 mL of water was stirred mechanically and heated at about 70° C. for 16 hours. The resulting clear yellow solution was cooled to about 60° C. and treated with 50 mL of concentrated HCl. The product precipitated from the solution and was isolated by filtration. Recrystallization from absolute ethanol gave the above named product as a beige crystalline solid in a yield of 24 g (54 percent of theoretical). The product melted at 114°-115° C.; 1H NMR (CDCl3): δ 1.17 (t, 3H, --CH3), 2.60-3.48 (m, 7H, ring protons and --CH2CH3), 5.05 (s, 2H, ArCH 2O--), 6.83-7.55 (m, 9H, ArH's), 18.1 (s, 1H, enol, H).

Workup

temperatureThe resulting clear yellow solution was cooled to about 60° C.
customThe product precipitated from the solution
customwas isolated by filtration
customRecrystallization from absolute ethanol
customgave the

Sources & evidence

ORD record: ord-d37651b084804dd0a59c24af45c42aef
Source dataset: uspto-grants-1991_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04983211

Reaction notes

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