Hydrochloric Acid → 5-(1-Hydroxyhexadecylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione

HRID 236472Notes

Reaction equation

[CH3:1][C:2]1([CH3:10])[O:7][C:6](=[O:8])[CH2:5][C:4](=[O:9])[O:3]1.N1C=CC=CC=1.[C:17](Cl)(=[O:33])[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32].Cl>ClCCl.C(Cl)(Cl)Cl>[CH3:1][C:2]1([CH3:10])[O:7][C:6](=[O:8])[C:5](=[C:17]([OH:33])[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])[C:4](=[O:9])[O:3]1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 2,2-dimethyl-1,3-dioxane-4,6-dione (Meldrum's acid, 72 g) in dichloromethane (1 l) was added pyridine (81 ml). Then, palmitoyl chloride (150.7 g) was added thereto at 0° C. The mixture was stirred at 0° C. for 1 hour and for additional 2 hours at ambient temperature. The reaction mixture was diluted with chloroform (1 l), poured into ice water (1 l), acidified with dilute hydrochloric acid solution, and washed with water (500 ml×3). After drying over magnesium sulfate, the solvent was evaporated under reduced pressure to give 2,2-dimethyl-5-(1-hydroxyhexadecylidene)-1,3-dioxane-4,6-dione (200 g) as an oil.

Workup

customat 0° C
washwashed with water (500 ml×3)
dry with materialAfter drying over magnesium sulfate
customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record: ord-edcd776523f848a5af2621b84f6a06a4
Source dataset: uspto-grants-1987_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04643990

Reaction notes

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