Hydrochloric Acid → Methyl (1,2-benzoxazol-3-yl)acetate

HRID 378550

Reaction equation

HRID 378550 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[C:3]([CH2:10][C:11]([OH:13])=[O:12])=[N:2]1.[CH3:14]COCC.Cl>CO>[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[C:3]([CH2:10][C:11]([O:13][CH3:14])=[O:12])=[N:2]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 3017292-(1,2-Benzoxazol-3-yl)acetic acid

Product 1

HCID 2763403Methyl (1,2-benzoxazol-3-yl)acetate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 1,2-benzisoxazole-3-acetic acid (prepared according to G. Casini et al, J. Het. Chem. 6, 1969, 279) (18 g), ether saturated with dry HCl (150 ml) and methanol (200 ml) was stirred for 2 h at room temperature. Removal of the volatiles in vacuo gave methyl 1,2-benzisoxazole-3-acetate (17 g) as an oil. The oil was dissolved in tetrahydrofuran (100 ml) and added dropwise to a suspension of lithium aluminium hydride (6 g) in tetrahydrofuran (200 ml) at 0-10° C. followed by stirring for 30 min at 15° C. Usual work-up gave 2-(1,2-benzisoxazol-3-yl)ethanol (13 g) as an oil.

Workup

  1. customRemoval of the volatiles in vacuo

Sources & evidence

ORD record
ord-ad19e0b454cd4ddc81a13c4262240dd0
Source dataset
uspto-grants-2000_02
Patent number
US06031099

Linked notes

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