Methyl 4-hydroxy-2-methoxybenzoate → 4-(2-Tert-butoxycarbonylethyl)-2-methoxybenzoic acid

HRID 1676122Notes

Reaction equation

HRID 1676122 reaction equation
[C:1]([O:5][C:6]([CH2:8][CH2:9][C:10]1[C:18](C)=[CH:17][C:13]([C:14]([OH:16])=[O:15])=[CH:12][C:11]=1C)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:21][O:22]C(=O)C1C=CC(O)=CC=1OC>>[C:1]([O:5][C:6]([CH2:8][CH2:9][C:10]1[CH:11]=[CH:12][C:13]([C:14]([OH:16])=[O:15])=[C:17]([O:22][CH3:21])[CH:18]=1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

3

Reactant 2

HCID 12532676Methyl 4-hydroxy-2-methoxybenzoateHCID 594979324-(2-Tert-butoxycarbonyl-ethyl)-3,5-dimethyl-benzoic acid

Product 1

HCID 594979244-(2-Tert-butoxycarbonylethyl)-2-methoxybenzoic acid

Procedure

The title compound is prepared in analogy to 4-(2-tert-butoxycarbonyl-ethyl)-3,5-dimethyl-benzoic acid starting from 4-hydroxy-2-methoxy-benzoic acid methyl ester; LC-MS: tR=0.94 min, [M+1]+=281.23; 1H NMR (CDCl3): δ 1.34 (s, 9 H), 2.40-2.47 (m, 2 H), 2.76-2.85 (m, 2 H), 3.83 (s, 3 H), 7.21-7.28 (dd, J=7.6, 3.2 Hz, 1 H), 7.41-7.49 (m, 2 H).

Sources & evidence

ORD record
ord-6ac33a33619e4387a70beb16da1739ed
Source dataset
uspto-grants-2011_08
Patent number
US08003800B2

Reaction notes

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