ChemicalBook CAS DataBase List (4-BENZYLOXY-3-CHLORO-PHENYL)-METHANOL

(4-BENZYLOXY-3-CHLORO-PHENYL)-METHANOL synthesis

5synthesis methods

Product Name:(4-BENZYLOXY-3-CHLORO-PHENYL)-METHANOL
CAS Number:536974-87-5
Molecular formula:C14H13ClO2
Molecular Weight:248.7

4-BENZYLOXY-3-CHLORO-BENZOIC ACID METHYL ESTER

536974-86-4
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536974-87-5
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Yield:536974-87-5 97%

Reaction Conditions:

Stage #1: 4-benzyloxy-3-chloro-benzoic acid methyl esterwith lithium aluminium tetrahydride in tetrahydrofuran at 20; for 0.5 h;
Stage #2: with sodium hydroxide;water in tetrahydrofuran; for 0.333333 h;

Steps:

(4-Benzyloxy-3-chloro-phenyl)-methanol (CAB02127) A solution of 4-benzyloxy-3-chloro-benzoic acid methyl ester (CAB02121, 4.15 g, 15.0 mmol) in THF (30 mL) was added slowly with a syringe to a suspension of lithium aluminium hydride (1.0 g, 26.3 mmol) in THF (30 mL). The reaction mixture was stirred for 30 minutes at room temperature and then carefully quenched by addition of 2N sodium hydroxide solution in water. After 20 minutes stirring the colour of the mixture turned from grey to white. The white precipitate was filtered off, the filtrate was dried over sodium sulphate and concentrated under reduced pressure to give an colourless oil, which was used without further purification. Yield: 3.61 g (97%). ¹H-NMR (400 MHz, CDCl₃) δ=2.12 (s, 1H, -OH), 4.56 (s, 2H), 5.16 (s, 2H), 6.93 (d, J=8.6 Hz, 1H), 7.14 (dd, J=8.6, 2.3 Hz, 1H), 7.31-7.48 (m, 6H).

References:

US2004/19016,2004,A1 Location in patent:Page/Page column 56

66422-84-2 Synthesis