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

HRID 272194Notes

Reaction equation

HRID 272194 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-f030c0e328744626b6a9d1e4a949d794
Source dataset
uspto-grants-2008_11
Patent number
US07452901B2

Reaction notes

Loading…