Water → HCID 15617911, compound

HRID 1165020Notes

Reaction equation

HRID 1165020 reaction equation
[C:1]1([CH2:7][C:8]2[CH:17]=[CH:16][C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:9]=2[O:18][CH3:19])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[S:20](=O)(=[O:23])([OH:22])[OH:21].O.C(=O)(O)[O-].[Na+]>CCCCCC.C(OCC)(=O)C.C(OCC)(=O)C>[CH3:19][O:18][C:9]1[C:10]2[C:15](=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:16]([S:20]([OH:23])(=[O:22])=[O:21])=[CH:17][C:8]=1[CH2:7][C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

7

Reactant 4

HCID 962WaterHCID 1118Sulfuric AcidHCID 516892Sodium BicarbonateHCID 15617899HCID 15617899, compound

Product 1

HCID 15617911HCID 15617911, compoundYield 52%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 21226206Ethyl acetate hexaneSolvent

Procedure

The product of Example 94 Part A (3.0 g, 0.012 mole) was added in portions to concentrated sulfuric acid (10 ml) at -10°. The mixture was stirred at -10° for 2 hours and poured into water. Sodium bicarbonate (1.0 g) was added, and the crude product was isolated by extraction with ethyl acetate. The title compound (2.0 g, 52%) was obtained as a brown oil after chromatography (1:1 hexane/ethyl acetate; then 99:1 ethyl acetate/acetic acid; then methanol).

Sources & evidence

ORD record
ord-c64f2eaa96ca49809c5c33b707b8226e
Source dataset
uspto-grants-1990_03
Patent number
US04906636

Reaction notes

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