Hydrochloric Acid → HCID 18977789, compound

HRID 2392976Notes

Reaction equation

[CH3:1][C:2]1[CH:17]=[CH:16][C:5]([C:6]([O:8][C:9]2[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=2)=[O:7])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][OH:36].Cl>CN(C)C=O>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([O:8][C:9]2[CH:14]=[CH:13][C:12]([O:15][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][OH:36])=[CH:11][CH:10]=2)=[O:7])=[CH:16][CH:17]=1

Participants

Conditions

Temperature: 80 °C

Procedure

9.3 g (0.042 mol) of 4-hydroxyphenyl 4-methylbenzoate are dissolved in 80 ml of absolute dimethylformamide (DMF), and 6.8 g (0.05 mol) of potassium carbonate are added. 11.3 g (0.045 mol) of 11-bromo-1-undecanol are then added, and the mixture is heated at 80° C. for 24 hours. During this time, a further 0.6 g of potassium carbonate is added. For work-up, the reaction mixture is poured into ice water and acidified by means of dilute hydrochloric acid, and the precipitate is filtered off with suction. The residue is dissolved in ethyl acetate, washed with water, dried over sodium sulfate and freed from solvent under reduced pressure. The product is purified by column chromatography (silica gel, eluent toluene/ethyl acetate 5:1).

Workup

filtrationthe precipitate is filtered off with suction
dissolutionThe residue is dissolved in ethyl acetate
washwashed with water
dry with materialdried over sodium sulfate
customThe product is purified by column chromatography (silica gel, eluent toluene/ethyl acetate 5:1)

Sources & evidence

ORD record: ord-a975f39cf89e4bcf8eee5a1867457891
Source dataset: uspto-grants-1998_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05804097

Reaction notes

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