Sulfuric Acid → HCID 66586249, compound

HRID 635410Notes

Reaction equation

OC[C@@H]([C@H]([C@@H]([C@@H](CO)O)O)O)O.[CH3:13][C:14]1[CH:15]=[C:16]([CH:19]=[CH:20][C:21]=1[CH3:22])[CH:17]=O.S(=O)(=O)(O)O.[CH3:28][C:29]1[CH:30]=[C:31]([CH:45]=[CH:46][C:47]=1[CH3:48])[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]>>[CH3:13][C:14]1[CH:15]=[C:16]([CH:19]=[CH:20][C:21]=1[CH3:22])[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]([CH3:48])=[C:29]([CH3:28])[CH:30]=1)[OH:34]

Participants

Reactant 4

HCID 1118Sulfuric Acid

HCID 5780Sorbitol

HCID 222783,4-Dimethylbenzaldehyde

HCID 66615073HCID 66615073, compound

Product 1

HCID 66586249HCID 66586249, compoundYield 0.5%

Conditions

Temperature: 21 °C

Procedure

A 500 ml four-necked flask was charged with a 70 wt % aqueous solution of 143 g (0.55 mole) of D-sorbitol, 73.7 g (0.55 mole) of 3,4-dimethylbenzaldehyde and 12 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-dimethylbenzylidene)-D-sorbitol was produced in a yield of 70% and 0.5% or less of bis(3,4-dimethylbenzylidene)-D-sorbitol was also produced.

Workup

customThe obtained reaction mixture

Sources & evidence

ORD record: ord-5dbe194dc6004a01bf678de18e6b6847
Source dataset: uspto-grants-2001_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06187842B1

Reaction notes

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