1-[4-(3-bromopropoxy)-2-hydroxy-3-propylphenyl]ethanone → HCID 14405940, compound

HRID 1650255Notes

Reaction equation

HRID 1650255 reaction equation
[SH:1][CH2:2][CH:3]1[O:7][C:6]([CH2:15][CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])([CH2:8][CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])[S:5][CH2:4]1.[CH2:22]([C:25]1[C:35]([OH:36])=[C:34]([C:37](=[O:39])[CH3:38])[CH:33]=[CH:32][C:26]=1[O:27][CH2:28][CH2:29][CH2:30]Br)[CH2:23][CH3:24]>>[C:37]([C:34]1[CH:33]=[CH:32][C:26]([O:27][CH2:28][CH2:29][CH2:30][S:1][CH2:2][CH:3]2[O:7][C:6]([CH2:8][CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])([CH2:15][CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])[S:5][CH2:4]2)=[C:25]([CH2:22][CH2:23][CH3:24])[C:35]=1[OH:36])(=[O:39])[CH3:38]

Participants

3

Reactant 2

HCID 27752211-[4-(3-bromopropoxy)-2-hydroxy-3-propylphenyl]ethanoneHCID 14405955HCID 14405955, compound

Product 1

HCID 14405940HCID 14405940, compound

Procedure

The title compound was prepared according to the procedure of Example 2 using the mercaptan produced in Example 64 (1.0 g, 0.003 mol), (3-(2-n-propyl-3-hydroxy-4-acetylphenoxy)-1-bromopropane (described in U.S. Pat. No. 4,565,882, Example 14) (1.1 g, 0.0033 mol) and anhydrous potassium carbonate (1.6 g) in methyl ethyl ketone (15 ml) The crude product was chromatographed on silica gel using 20% ethyl acetate/hexane as eluent to give 1.54 g (90%) of the product as an oil.

Workup

  1. custom4,565,882, Example 14) (1.1 g, 0.0033 mol) and anhydrous potassium carbonate (1.6 g) in methyl ethyl ketone (15 ml) The crude product was chromatographed on silica gel using 20% ethyl acetate/hexane as eluent

Sources & evidence

ORD record
ord-e8a8d69fae4b4f048b72256d799a3242
Source dataset
uspto-grants-1990_05
Patent number
US04923891

Reaction notes

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