4-Hydroxybenzoic Acid → (2R,5R)-2-(4'-pentyloxycarbonylphenoxy)-5-hexyl-delta-valerolactone

HRID 893252Notes

Reaction equation

HRID 893252 reaction equation
[OH:1][C@H:2]1[CH2:8][CH2:7][C@@H:6]([CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])[O:5][C:3]1=[O:4].O[C:16]1[CH:24]=[CH:23][C:19]([C:20]([OH:22])=[O:21])=[CH:18][CH:17]=1>>[CH2:8]([O:22][C:20]([C:19]1[CH:23]=[CH:24][C:16]([O:1][C@@H:2]2[CH2:8][CH2:7][C@@H:6]([CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])[O:5][C:3]2=[O:4])=[CH:17][CH:18]=1)=[O:21])[CH2:7][CH2:6][CH2:9][CH3:10]

Participants

3

Reactant 2

HCID 1354-Hydroxybenzoic AcidHCID 14645393(2S,5R)-hydroxy-5-hexyl-delta-valerolactone

Product 1

HCID 22844669(2R,5R)-2-(4'-pentyloxycarbonylphenoxy)-5-hexyl-delta-valerolactone

Procedure

A crude product was obtained in the same manner as described in Example 22 except that (2S,5R)-2-hydroxy-5-hexyl-δ-valerolactone was used in an amount of 125 mg and 125 mg of p-hydroxybenzoic acid was used instead of 120 mg of 4-octyloxy-3-cyanobenzoic acid. The crude product was purified by the silica gel column chromatography to obtain 20 mg of (2R,5R)-2-(4'-pentyloxycarbonylphenoxy)-5-hexyl-δ-valerolactone.

Workup

  1. customThe crude product was purified by the silica gel column chromatography

Sources & evidence

ORD record
ord-e713b1b560a54bbfb1323be7bcb1d575
Source dataset
uspto-grants-1992_06
Patent number
US05124069

Reaction notes

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