Catechol → HCID 61343388, compound

HRID 1917016Notes

Reaction equation

[C:1]1([C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[OH:4])[OH:2].S(C1C=CC(C)=CC=1)(O[CH2:13][CH:14]1[CH2:18][CH2:17][CH2:16][CH2:15]1)(=O)=O.C(=O)([O-])[O-].[K+].[K+]>>[CH:14]1([CH2:13][O:2][C:1]2[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=2[OH:4])[CH2:18][CH2:17][CH2:16][CH2:15]1

Participants

Reactant 3

HCID 289Catechol

HCID 11430Potassium Carbonate

HCID 12568544Cyclopentylmethyl 4-methylbenzene-1-sulfonate

Product 1

HCID 61343388HCID 61343388, compoundYield 44%

Procedure

This compound was prepared in 44% yield from catechol and cyclopentylmethyl tosylate according to the general procedure for 2p in Example IX, except that potassium carbonate was used in place of cesium carbonate. Yellow oil; 1H NMR (CDCl3): δ 1.33 (m, 2H), 1.58-1.69 (m, 4H), 1.82-1.89 (m, 2H), 2.40 (s-7, J=7.70 Hz, 1H), 3.91 (d, J=7.15 Hz, 2H), 5.66 (s, 1H), 6.81-6.88 (m, 3H), 6.92-6.94 (m, 1H); 13C NMR (CDCl3): δ 25.53, 29.54, 39.11, 73.20, 111.78, 114.49, 120.16, 121.40, 145.90, 146.16.

Sources & evidence

ORD record: ord-19552332aba7482ba1994278e73b1e87
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08618162B2

Reaction notes

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