Benzyl 4-Hydroxybenzoate → Benzoic acid, 4-[(2S)-oxiranylmethoxy]-, methyl ester

HRID 374485Notes

Reaction equation

[OH:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][CH:3]=1.OC1C=CC(C([O:19][CH2:20][C:21]2[CH:26]=CC=CC=2)=O)=CC=1.C1(C)C(S(OC[C@H]2OC2)(=O)=O)=CC=CC=1.C(C1OC1)Br>>[O:19]1[CH2:20][C@H:21]1[CH2:26][O:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:10][CH:11]=1

Participants

Reactant 4

HCID 7180Benzyl 4-Hydroxybenzoate

HCID 7456Methylparaben

HCID 18430Epibromohydrin

HCID 71369135[(2S)-Oxiran-2-yl]methyl 2-methylbenzene-1-sulfonate

Product 1

HCID 931644Benzoic acid, 4-[(2S)-oxiranylmethoxy]-, methyl esterYield 90%

Procedure

The same procedure of Reference Example 4 was repeated except that methyl 4-hydroxybenzoate was used in lieu of benzyl 4-hydroxybenzoate, and (S)-(+)-glycidyl toluenesulfonate was used in lieu of epibromohydrin to give the title compound (yield 90%).

Sources & evidence

ORD record: ord-ec2c56d6fc0942b09e2a5ff02e8d7cc0
Source dataset: uspto-grants-1996_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05480899

Reaction notes

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