Sodium Hydroxide → HCID 22381862, compound

HRID 895828Notes

Reaction equation

[OH-].[Na+].S(Cl)(Cl)=O.[Cl:7][S:8]([OH:11])(=O)=[O:9].[CH2:12]([O:15][C:16]1[CH:24]=[CH:23][CH:22]=[CH:21][C:17]=1[C:18]([OH:20])=[O:19])[CH2:13][CH3:14]>ClCCl>[Cl:7][S:8]([C:22]1[CH:23]=[CH:24][C:16]([O:15][CH2:12][CH2:13][CH3:14])=[C:17]([CH:21]=1)[C:18]([OH:20])=[O:19])(=[O:11])=[O:9]

Participants

Conditions

Temperature: -10 °C

Procedure

A three-neck flask, equipped with a 5M aqueous sodium hydroxide scrub (550 ml), was charged with thionyl chloride (40 ml, 0.55 mol) and chlorosulphonic acid (150 ml, 2.26 mol) and the stirred mixture cooled to about −10° C. A solution of 2-n-propoxybenzoic acid (100 g, 0.55 mol) in dichloromethane (200 ml) was added over 20 minutes, ensuring that the reaction temperature was maintained below 5° C., then the reaction mixture was allowed to warm to room temperature. The resulting solution was added over 1 hour to stirred, ice-cold water, whilst maintaining the temperature at about 0° C., and stirring continued for a further 30 minutes. The mixture was filtered and the solid thus obtained was washed with cold water (100 ml) and dried under vacuum to give the title compound (122.2 g, 80%) as a white solid. δ (DMSOd6): 1.13 (3H, t), 2.00 (2H, m), 4.32 (2H, t), 7.23 (1H, d), 8.21, (1H, m), 8.82 (1H, d).

Workup

temperaturewas maintained below 5° C.
temperatureto warm to room temperature
additionThe resulting solution was added over 1 hour
temperatureice-cold water, whilst maintaining the temperature at about 0° C.
stirringstirring
filtrationThe mixture was filtered
customthe solid thus obtained
washwas washed with cold water (100 ml)
customdried under vacuum

Sources & evidence

ORD record: ord-7ac9b97eb791487e8460de5d4188fb5b
Source dataset: uspto-grants-2005_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06916927B2

Reaction notes

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