Acetic Anhydride → HCID 70250978, compound

HRID 1595117Notes

Reaction equation

[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]([C:29]([OH:31])=[O:30])[CH2:9][CH2:10][CH2:11][CH2:12][S:13][CH2:14][CH2:15][CH2:16][CH2:17][CH:18]([C:26]([OH:28])=[O:27])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[OH:25].[CH3:32][C:33](OC(C)=O)=[O:34].[CH3:39][CH2:40][O:41]C(C)=O>>[C:33]([O:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]([C:29]([OH:31])=[O:30])[CH2:9][CH2:10][CH2:11][CH2:12][S:13][CH2:14][CH2:15][CH2:16][CH2:17][CH:18]([C:26]([OH:28])=[O:27])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[O:25][C:40](=[O:41])[CH3:39])(=[O:34])[CH3:32]

Participants

Reactant 3

HCID 7918Acetic Anhydride

HCID 8857Ethyl Acetate

HCID 70250424HCID 70250424, compound

Product 1

HCID 70250978HCID 70250978, compound

Procedure

2-Acetoxyphenyl-5-carboxypentyl sulfide (140) was prepared by the acetylation of 135 with Ac2O (FIG. 2Q). The title compound was obtained as a white solid (0.82 g, 87%) upon purification by chromatography on silica gel (EtOAc:hexanes, 20:80, then 40:60). 1H NMR (CDCl3) δ7.35-7.38 (m, 1 H, ArH), 7.19-7.23 (m, 2 H, ArH), 7.03-7.06 (m, 1 H, ArH), 2.85-2.89 (t, 2 H, J=7.1 Hz, CH2), 2.33-2.38 (t merged with a s, 5 H, J=7.2 Hz, CH2 and CH3), 1.60-1.70 (m, 4 H, CH2), 1.44-1.52 (m, 2 H, CH2).

Sources & evidence

ORD record: ord-6572d16cb8f245e0ba0220b425bc79e4
Source dataset: uspto-grants-2001_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06284918B1

Reaction notes

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