Reaction #2045059

Reaction equation

Benzyloxy acetyl chloride

2-(6-Hydroxynaphthalen-2-yl)-propionic acid methyl ester

triethylamine

→

99

Yield 63.9%

2-[6-(2-Benzyloxyacetoxy)naphthalen-2-yl]propionic acid methyl ester

Yield 63.9%

Solvents

acetone

Conditions

Workup

1. 1
   FiltrationSolids were filtered off
2. 2
   workup.DISTILLATIONacetone distilled off
3. 3
   workup.ADDITIONwater (100 ml) added
4. 4
   ExtractionCrude 99 was extracted into chloroform
5. 5
   Washwashed with 5% sodium bicarbonate (2×50 ml), water (2×50 ml)
6. 6
   Dryingdried over sodium sulphate
7. 7
   workup.DISTILLATIONdistilled
8. 8
   OtherCrude 99 was purified
9. 9
   Otherby recrystallising in chloroform:hexane (1:6)

Procedure

Benzyloxy acetyl chloride (24 gm, 86.95 mmol) was added drop-wise to a mixture of 2-(6-Hydroxynaphthalen-2-yl)-propionic acid methyl ester 6 (20 g, 86.95 mmol) and triethylamine (22.5 g, 222.35 mmol) in acetone (300 ml) and stirred for 2 hrs at room temp. Solids were filtered off, acetone distilled off, and water (100 ml) added. Crude 99 was extracted into chloroform, washed with 5% sodium bicarbonate (2×50 ml), water (2×50 ml), dried over sodium sulphate and distilled. Crude 99 was purified by recrystallising in chloroform:hexane (1:6) to get pure 99 (21 g, 63.9%) as a white powder. M.p: 58-60° C.

Source