4-chloro-3-(hydroxymethyl)phenol synthesis
- Product Name:4-chloro-3-(hydroxymethyl)phenol
- CAS Number:876299-47-7
- Molecular formula:C7H7ClO2
- Molecular Weight:158.58
56961-30-9
876299-47-7
General procedure for the synthesis of 4-chloro-3-(hydroxymethyl)phenol from 2-chloro-5-hydroxybenzoic acid: to a solution of 2-chloro-5-hydroxybenzoic acid (4 g, 23.2 mmol) in tetrahydrofuran (200 mL) was slowly added lithium aluminum hydride (1 M in ether, 25 mL, 25 mmol) under ice bath cooling conditions. The reaction mixture was heated to reflux for 6 hours. Upon completion of the reaction, the reaction mixture was diluted with a mixture of tetrahydrofuran and water, followed by acidification with 1M hydrochloric acid to acidity. Extraction was carried out with ethyl acetate and the organic phases were combined and dried over anhydrous sodium sulfate. The organic phase was concentrated under reduced pressure to give 4.3 g of 4-chloro-3-(hydroxymethyl)phenol in quantitative yield.
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Yield:876299-47-7 100%
Reaction Conditions:
with lithium aluminium tetrahydride in tetrahydrofuran;diethyl ether at 0; for 6 h;Heating / reflux;
Steps:
26 4-Chloro-3-hydroxymethyl-phenol
Lithium aluminium hydride (1M in diethyl ether, 25 mL, 25 mmol) was added to an ice-cooled solution of 2-chloro-5-hydroxy-benzoic acid (4 g, 23.2 mmol) in tetrahydrofuran (200 mL) and the mixture was heated under reflux for 6 hours. The mixture was then diluted with a mixture of water/tetrahydrofuran, acidified with 1M hydrochloric acid, and extracted with ethyl acetate. The organic solution was dried over sodium sulphate and concentrated in vacuo to afford the title compound in quantitative yield, 4.3 g.
References:
US2006/35922,2006,A1 Location in patent:Page/Page column 31