4-Hydroxybenzyl Alcohol → Butanoic acid, 4-[4-(hydroxymethyl)phenoxy]-, ethyl ester

HRID 888052Notes

Reaction equation

HRID 888052 reaction equation
[OH:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([OH:9])=[CH:5][CH:4]=1.Br[CH2:11][CH2:12][CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15]>>[OH:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([O:9][CH2:11][CH2:12][CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:5][CH:4]=1

Participants

3

Reactant 2

HCID 1254-Hydroxybenzyl AlcoholHCID 76300Ethyl 4-bromobutyrate

Product 1

HCID 22340602Butanoic acid, 4-[4-(hydroxymethyl)phenoxy]-, ethyl ester

Procedure

Ethyl 4-(4-(hydroxymethyl)phenoxy)butanoate 29b was prepared by reacting 4-(hydroxymethyl)phenol 27b with ethyl 4-bromobutyrate 28b according to protocol described for the compound 29a in Example 24 (Scheme 9). The ester 29b was isolated as colorless oil 96% yield (2.26 g). 1H NMR (400 MHz, CDCl3): δ 1.24 (3H, t, J=7.2 Hz); 2.07 (2H, m); 2.15 (2H, t, J=7.2 Hz)); 3.97 (2H, t, J=6.4 Hz); 4.10 (2H, q, J=7.2 Hz); 4.59 (2H, s); 6.88 (1H, s); 6.87 (1H, s); 7.24-7.27 (2H, m).

Workup

  1. customEthyl 4-(4-(hydroxymethyl)phenoxy)butanoate 29b was prepared

Sources & evidence

ORD record
ord-770f6b481490452e93da2d2f263db183
Source dataset
uspto-grants-2012_08
Patent number
US08247563B2

Reaction notes

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