Ammonium Chloride → HCID 10020919, compound

HRID 1493022Notes

Reaction equation

[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6]Cl.[CH3:8][C:9]([C:12]1[CH:13]=[C:14]([CH:19]=[C:20]([C:23]([CH3:26])([CH3:25])[CH3:24])[C:21]=1[OH:22])[C:15]([O:17][CH3:18])=[O:16])([CH3:11])[CH3:10].C(N(C(C)C)CC)(C)C.[NH4+].[Cl-]>C(Cl)Cl>[CH3:11][C:9]([C:12]1[CH:13]=[C:14]([CH:19]=[C:20]([C:23]([CH3:26])([CH3:25])[CH3:24])[C:21]=1[O:22][CH2:6][O:5][CH2:4][CH2:3][O:2][CH3:1])[C:15]([O:17][CH3:18])=[O:16])([CH3:8])[CH3:10]

Participants

Conditions

Temperature: 25 °C

Procedure

2-Methoxyethoxymethyl chloride (24.0 g, 192.7 mmol) is added dropwise to a 0° C. mixture of 25.0 g (94.6 mmol) of 3,5-bis(1,1-dimethylethyl)-4-hydroxybenzoic acid, methyl ester and 27.5 g (212.4 mmol) of diisopropylethylamine in 50 ml of CH2Cl2 under a nitrogen atmosphere. The reaction is stirred at 25° C. for 24 hours and then poured onto saturated aqueous NH4Cl and the layers are separated. The aqueous layer is extracted with t-butylmethylether (2×150 ml). The combined organic extracts are washed with saturated aqueous NH4Cl, water and brine (2×), dried over Na2SO4, and concentrated in vacuo to give 33.2 g of the desired product as an orange oil. The product is pure enough to use in subsequent reactions. A sample can be purified by chromatography (flash, SiO2, 230-400 mesh, 29×6.5 cm, 15% t-butylmethylether-hexane) followed by Kugelrohr distillation.

Workup

customthe layers are separated
extractionThe aqueous layer is extracted with t-butylmethylether (2×150 ml)
washThe combined organic extracts are washed with saturated aqueous NH4Cl, water and brine (2×)
dry with materialdried over Na2SO4
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-24ae68743b534be485a64b4c6e2c03a0
Source dataset: uspto-grants-1994_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05376670

Reaction notes

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