4-Hydroxybenzaldehyde → Benzaldehyde, 4-(2-hydroxyethoxy)-

HRID 1269476Notes

Reaction equation

[OH:1][CH2:2][CH2:3][O:4][C:5]1[CH:12]=[CH:11][C:8]([CH:9]=C)=[CH:7][CH:6]=1.[OH:13]C1C=CC(C=O)=CC=1>>[OH:1][CH2:2][CH2:3][O:4][C:5]1[CH:12]=[CH:11][C:8]([CH:9]=[O:13])=[CH:7][CH:6]=1

Participants

Reactant 2

HCID 1264-Hydroxybenzaldehyde

HCID 149378112-(4-Vinylphenoxy)ethanol

Product 1

HCID 89178Benzaldehyde, 4-(2-hydroxyethoxy)-

Procedure

Woods et al. (U.S. Pat. No. 5,019,629) describe a two-step procedure for preparing p-(2-hydroxyethoxy)styrene starting with p-hydroxybenzaldehyde. In the first step, p-(2-hydroxyethoxy)benzaldehyde is formed by reacting p-hydroxybenzaldehyde with ethylene carbonate in the presence of potassium carbonate. In the second step, p-(2-hydroxyethoxy)styrene is formed by reacting the isolated p-(2-hydroxyethoxy)benzaldehyde with methyltriphenylphosphonium bromide in the presence of sodium amide.

Sources & evidence

ORD record: ord-f70bfa49f7e64fe7968c69edea5b4b7f
Source dataset: uspto-grants-2007_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07199272B2

Reaction notes

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