Potassium Hydroxide → (+/-)-2-(2(1-Naphthyl)benzyl)propionic acid

HRID 1106960

Reaction equation

[CH3:1][CH:2]([C:7](OC)=O)[C:3]([O:5]C)=[O:4].[Na].[C:12]1([C:22]2[CH:29]=[CH:28][CH:27]=[CH:26][C:23]=2CBr)[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:15]=[CH:14][CH:13]=1.[OH-].[K+]>O>[C:12]1([C:22]2[CH:29]=[CH:28][CH:27]=[CH:26][C:23]=2[CH2:7][CH:2]([CH3:1])[C:3]([OH:5])=[O:4])[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:15]=[CH:14][CH:13]=1

Participants

Conditions

Temperature: 130 °C

Procedure

75 g (0.43 mmol) of dimethyl methylmalonate dissolved in 50 cm3 of H2O-free EtOH are added dropwise at room temperature to 10 g (0.43 mmol) of sodium in 100 cm3 of H2O-free EtOH. Subsequently, 140 g (0.43 mmol) of 7 in 200 cm3 of H2O-free EtOH were added dropwise and the mixture was heated under reflux for 3 hours. 85 g (1.3 mol) of KOH dissolved in 100 cm3 of H2O were added at room temperature and the mixture was heated under reflux for a further 4 hours. The solvents were removed under reduced pressure, the residue was admixed with H2O until completely dissolved and acidified with concentrated aqueous HCl to a pH of 1. The precipitate formed was filtered off with suction, dried and heated at 130° C. for 1 hour. This gave 96 g (77%) of 8 as a viscous oil.

Workup

temperaturethe mixture was heated
temperatureunder reflux for 3 hours
additionwere added at room temperature
temperaturethe mixture was heated
temperatureunder reflux for a further 4 hours
customThe solvents were removed under reduced pressure
dissolutionuntil completely dissolved
customThe precipitate formed
filtrationwas filtered off with suction
customdried

Sources & evidence

ORD record: ord-1cafda4585aa4707b7f59b1ddd7dff31
Source dataset: uspto-grants-2000_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06057408

Linked notes

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