4-Hydroxybenzaldehyde → Ethyl 2-(4-formylphenoxy)acetate

HRID 592078Notes

Reaction equation

C([C:3]1[CH:4]=[C:5]([CH:13]=[CH:14][CH:15]=1)[O:6][CH2:7][C:8]([O:10][CH2:11][CH3:12])=[O:9])=O.[OH:16][C:17]1C=CC(C=O)=CC=1.BrCC(OCC)=O>>[CH:17]([C:15]1[CH:3]=[CH:4][C:5]([O:6][CH2:7][C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:13][CH:14]=1)=[O:16]

Participants

Reactant 3

HCID 1264-Hydroxybenzaldehyde

HCID 7748Ethyl bromoacetate

HCID 1494377Ethyl 2-(3-formylphenoxy)acetate

Product 1

HCID 291358Ethyl 2-(4-formylphenoxy)acetateYield 52%

Procedure

In an analogous manner to compound 47, 4-hydroxy benzaldehyde (1 eq) and ethyl 2-bromoacetate (1.1 eq) were reacted to produce the desired product (52%) as a brown oil. NMR: δ 1.306 (t, J=6.8 Hz, 3H), 4.29 (q, J=7.2 Hz, 2H), 4.710 (s, 2H), 7.016 (d, J=8.8 Hz, 2H), 7.85 (d, J=8.8 Hz, 2H), 9.904 (s, 1H).

Sources & evidence

ORD record: ord-59bc3005954b46c68ba4a16f0db44d4e
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09238656B2

Reaction notes

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