2-Chloroethanol → Mandelic acid, 2-chloroethyl ester

HRID 1656719Notes

Reaction equation

[OH:1][CH:2]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[C:3]([OH:5])=[O:4].[Cl:12][CH2:13][CH2:14]O>>[OH:1][CH:2]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[C:3]([O:5][CH2:14][CH2:13][Cl:12])=[O:4]

Participants

Reactant 2

HCID 342-Chloroethanol

HCID 1292Mandelic Acid

Product 1

HCID 252572Mandelic acid, 2-chloroethyl ester

Procedure

2-Chloroethyl 2-hydroxy-2-phenylacetate was prepared from 2-hydroxy-2-phenylacetic acid and excess 2-chloroethanol essentially by the method described in Step 1 of Example 1; however, the distillate solidified after standing at 4° C.: b.p. 119° C./0.35 mm Hg; m.p. 43°-45° C.; 1H NMR δ 3.50 (d, 1H, J=6.0 Hz), δ 3.58-3.62 (m, 2H), δ 4.28-4.46 (m, 2H),δ 5.22 (d, 1H, J=5.9 Hz), δ 7.3-7.4 (5H); HRMS calcd for C9H7ClO3Tms (M--CH3) 271.0557, obsd 271.0598.

Workup

customafter standing at 4° C.

Sources & evidence

ORD record: ord-36fb6998a22b45ecafa5c648004ca06f
Source dataset: uspto-grants-1993_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05254718

Reaction notes

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