2',4'-Dihydroxyacetophenone → 2'-Hydroxy-4'-(ethoxycarbonyldimethylmethoxy)acetophenone

HRID 549455Notes

Reaction equation

HRID 549455 reaction equation
[OH:1][C:2]1[CH:7]=[C:6]([OH:8])[CH:5]=[CH:4][C:3]=1[C:9](=[O:11])[CH3:10].Br[C:13]([CH3:20])([CH3:19])[C:14]([O:16][CH2:17][CH3:18])=[O:15]>>[OH:1][C:2]1[CH:7]=[C:6]([O:8][C:13]([C:14]([O:16][CH2:17][CH3:18])=[O:15])([CH3:20])[CH3:19])[CH:5]=[CH:4][C:3]=1[C:9](=[O:11])[CH3:10]

Participants

3

Reactant 2

HCID 69902',4'-DihydroxyacetophenoneHCID 11745Propanoic acid, 2-bromo-2-methyl-, ethyl ester

Product 1

HCID 577628812'-Hydroxy-4'-(ethoxycarbonyldimethylmethoxy)acetophenone

Procedure

This compound was synthesized from 2′,4′-dihydroxyacetophenone and ethyl bromoisobutyrate (1 eq) according to general method 4 described earlier. It was purified by chromatography on silica gel (elution:cyclohexane/ethyl acetate 9:1). 1H NMR CDCl3 δppm: 1.25 (t, J=7.17 Hz, 3H), 1.67 (s, 6H), 2.56 (s, 3H), 4.24 (q, J=7.17 Hz, 2H), 6.27 (d, J=2.55 Hz, 1H), 6.37 (dd, J=2.55 Hz, J=8.72 Hz, 1H), 7.62 (d, J=8.72 Hz, 1H), 12.6 (signal, 1H).

Workup

  1. customIt was purified by chromatography on silica gel (elution:cyclohexane/ethyl acetate 9:1)

Sources & evidence

ORD record
ord-52719b0f72514b8ca3c2da286b02bfb5
Source dataset
uspto-grants-2011_05
Patent number
US07943661B2

Reaction notes

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