4-Butylphenol → HCID 10156979, compound

HRID 459122Notes

Reaction equation

[OH:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][C@H:13]([O:17][CH3:18])[C:14]([OH:16])=[O:15])=[CH:8][CH:7]=1.[CH3:19][CH2:20][CH2:21][CH2:22][C:23]1[CH:24]=[CH:25][C:26](O)=[CH:27][CH:28]=1>>[CH2:22]([C:23]1[CH:24]=[CH:25][C:26]([O:1][CH2:2][CH2:3][CH2:4][O:5][C:6]2[CH:11]=[CH:10][C:9]([CH2:12][C@H:13]([O:17][CH3:18])[C:14]([OH:16])=[O:15])=[CH:8][CH:7]=2)=[CH:27][CH:28]=1)[CH2:21][CH2:20][CH3:19]

Participants

Reactant 2

HCID 154204-Butylphenol

HCID 69424952(2S)-3-[4-(3-Hydroxy-propoxy)-phenyl]-2-methoxy-propionic acid

Product 1

HCID 10156979HCID 10156979, compound

Procedure

The title compound was prepared from (2S)-3-[4-(3-hydroxy-propoxy)-phenyl]-2-methoxy-propionic acid linked to Wang's Resin (Example 94, Step D) via Mitsunobu coupling with 4-n-butylphenol and cleavage from the resin (Standard Procedure G) gave an oily solid (7%). 1H-NMR (200.15 MHz, CDCl3): δ 7.11 (dd, 4H, J=12.7, 8.6), 6.82 (dd, 4H, J=8.6, 3.2), 4.12 (t, 4H, J=6.2), 3.97 (dd, 1H, J=7.7, 4.4), 3.38 (s, 3H), 3.30 (dd, 1H, J=14.5, 4.4), 2.94 (dd, 1H, J=14.5, 7.7), 2.54 (t, 2H, J=7.7), 2.23 (qn, 2H, J=6.2), 1.63–1.48 (m, 2H), 1.42–1.24 (m, 2H), 0.91 (t, 3H, J=7.2).

Sources & evidence

ORD record: ord-f5eb60a004734f84b5fd617a4c193efe
Source dataset: uspto-grants-2007_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07192982B2

Reaction notes

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