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Dodecanedioic acid, 1-(phenylmethyl) ester synthesis
- Product Name:Dodecanedioic acid, 1-(phenylmethyl) ester
- CAS Number:88353-04-2
- Molecular formula:C19H28O4
- Molecular Weight:320.42
Yield: 45%
Reaction Conditions:
with potassium carbonate in N,N-dimethyl-formamide at 80; for 4 h;
Steps:
1 Step1. Preparation of 12-(benzyloxy)-12-oxododecanoic acid 76
To a solution of dodecanedioic acid (74) (21.0 g, 91.3 mmol) in DMF (200 ml) was added potassium carbonate (10 g, 72.4 mmol) and benzyl bromide (75) (10 ml, 84.2 mmol). The solution was stirred at 80oC for 4 hours, cooled to 0oC then carefully acidified with 6M HCl. Dilute with water (250 ml) and extract with ethyl acetate (500ml). The ethyl acetate extract was washed with brine (3 x 250 ml), dried on magnesium sulfate, filtered and concentrated to dryness. The solid was suspended in dichloromethane (200 ml) and filtered. The filtrate, which was now enriched in the product, was concentrated then purified by column chromatography on silica gel 60 (Gradient: 0 to 10% methanol in DCM) to afford 12-(benzyloxy)-12-oxododecanoic acid (76) as a colorless solid (13 g, 45 %). Structure confirmed by mass spectroscopy
References:
ARBUTUS BIOPHARMA CORPORATION;HEYES, James;HOLLAND, Richard J.;PALMER, Lorne Ralph;WOOD, Mark WO2020/93053, 2020, A1 Location in patent:Page/Page column 67; 70