6-Hydroxy-3-methyl-4-vinyl-phthalic Acid Dimethyl Ester → 4-Ethyl-6-hydroxy-3-methyl-phthalic Acid Dimethyl Ester

HRID 33002Notes

Reaction equation

HRID 33002 reaction equation
[CH3:1][O:2][C:3](=[O:18])[C:4]1[C:5](=[C:10]([CH3:17])[C:11]([CH:15]=[CH2:16])=[CH:12][C:13]=1[OH:14])[C:6]([O:8][CH3:9])=[O:7]>C1C=CC=CC=1.CCOC(C)=O>[CH3:1][O:2][C:3](=[O:18])[C:4]1[C:5](=[C:10]([CH3:17])[C:11]([CH2:15][CH3:16])=[CH:12][C:13]=1[OH:14])[C:6]([O:8][CH3:9])=[O:7]

Participants

4

Reactant 1

HCID 597944986-Hydroxy-3-methyl-4-vinyl-phthalic Acid Dimethyl Ester

Product 1

HCID 597944774-Ethyl-6-hydroxy-3-methyl-phthalic Acid Dimethyl EsterYield 88.4%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 8857Ethyl AcetateSolvent

Procedure

6-Hydroxy-3-methyl-4-vinyl-phthalic acid dimethyl ester (1.27 g, 5.11 mmol) was dissolved in benzene (10 mL) and EtOAc (10 mL). Tristriphenylphosphine rhodium chloride (150 mg) was added and the reaction was placed under an atmosphere of hydrogen. Stirring at room temperature was continued. After 14 hours, the solvents were removed in vacuo and the crude material was purified by silica gel chromatography to provide 1.14 g (88%) of the desired product as an off-white solid. 1H NMR (300 MHz, CDCl3): δ=1.19 (t, J=7.8 Hz, 3H), 2.10 (s, 3H), 2.60 (q, J=7.8 Hz, 2H), 3.89 (s, 6H), 6.87 (s, 1H), 10.79 (s, 1H) ppm.

Workup

  1. customthe solvents were removed in vacuo
  2. customthe crude material was purified by silica gel chromatography

Sources & evidence

ORD record
ord-e096510d2a2441cab7f88646720d1d3d
Source dataset
uspto-grants-2008_09
Patent number
US07427636B2

Reaction notes

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