Sulfuric Acid → HCID 67020547, compound
Reaction equation
OC[C@@H]([C@H]([C@@H]([C@@H](CO)O)O)O)O.[Cl:13][C:14]1[CH:15]=[C:16]([CH:19]=[CH:20][C:21]=1[Cl:22])[CH:17]=O.S(=O)(=O)(O)O.[Cl:28][C:29]1[CH:30]=[C:31]([CH:45]=[CH:46][C:47]=1[Cl:48])[CH:32]=[C:33]([C@@H:35]([C@H:37]([C@@H:39]([C@@H:41]([CH2:43][OH:44])[OH:42])[OH:40])[OH:38])[OH:36])[OH:34]>>[Cl:13][C:14]1[CH:15]=[C:16]([CH:19]=[CH:20][C:21]=1[Cl:22])[CH:17]=[C:43]([OH:44])[C@@H:41]([OH:42])[C@@H:39]([OH:40])[C@H:37]([OH:38])[C@@H:35]([OH:36])[C:33](=[CH:32][C:31]1[CH:45]=[CH:46][C:47]([Cl:48])=[C:29]([Cl:28])[CH:30]=1)[OH:34]Participants
Conditions
- Temperature
- 21 °C
Procedure
A 500 ml four-necked flask was charged with a 70 wt % aqueous solution of 52 g (0.20 mole) of D-sorbitol, 35.0 g (0.20 mole) of 3,4-dichlorobenzaldehyde and 6 g of 50 wt % sulfuric acid. The air inside the system was replaced with nitrogen gas. The contents of the flask were stirred at a temperature of 21° C. for 6 hours. The obtained reaction mixture was analyzed by GC. It was found that mono(3,4-dichlorobenzylidene)-D-sorbitol was produced in a yield of 70% and 0.5% or less of bis(3,4-dichlorobenzylidene)-D-sorbitol was also produced. After standing for 24 hours, the reaction mixture was neutralized for 2 hours using 8.6 g of potassium hydroxide, and filtered to obtain cake. The cake was dispersed in 150 ml of toluene and was filtered again. After drying at 100° C. under a pressure ranging from normal pressure to 5 mmHg for 7 hours, 19.7 g of 2,4-O-(3,4-dichlorobenzylidene)-D-sorbitol was obtained with a purity of 99.2% as measured by GC (yield 29.2%). The product had a melting point of 202 to 205° C.
Workup
- customThe obtained reaction mixture
Sources & evidence
- ORD record
- ord-c28de20f026748799b0e57cc4d920e06
- Source dataset
- uspto-grants-2001_02
- Patent number
- US06187842B1
Reaction notes
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