2-Chloroethanol → 2-Chloroethyl 2-hydroxy-2-methylbutyrate

HRID 1656715Notes

Reaction equation

HRID 1656715 reaction equation
[OH:1][C:2]([CH3:8])([CH2:6][CH3:7])[C:3]([OH:5])=[O:4].[Cl:9][CH2:10][CH2:11]O>>[OH:1][C:2]([CH3:8])([CH2:6][CH3:7])[C:3]([O:5][CH2:11][CH2:10][Cl:9])=[O:4]

Participants

3

Reactant 2

HCID 342-ChloroethanolHCID 95433(+-)-2-Hydroxy-2-methylbutyric acid

Product 1

HCID 189532202-Chloroethyl 2-hydroxy-2-methylbutyrate

Procedure

2-Chloroethyl 2-hydroxy-2-methylbutyrate was prepared from 2-hydroxy-2-methylbutyric acid and excess 2-chloroethanol essentially by the method described in Step 1 of Example 1: b.p. 108° C./20 mm Hg; 1H NMR δ 0.90 (t, 3H, J=7.4 Hz), δ 1.44 (s, 3H), δ ca. 1.70 (m, 1H), δ ca. 1.83 (m, 1H), δ 3.10 (s, 1H), δ 3.72 (t, 2H, J=5.6 Hz), δ 4.43 (dd, 2H, J=5.6 Hz and 1.5 Hz); HRMS calcd for C6H9ClO3Tms (M--CH3) 237.0714, obsd 237.0750.

Sources & evidence

ORD record
ord-ce784772af6646289d54f91967af82bc
Source dataset
uspto-grants-1993_10
Patent number
US05254718

Reaction notes

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