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

HRID 236472
Notes
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Reaction equation

HRID 236472 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 8206Palmitoyl chlorideHCID 162492,2-Dimethyl-1,3-dioxane-4,6-dione

Product 1

HCID 546979555-(1-Hydroxyhexadecylidene)-2,2-dimethyl-1,3-dioxane-4,6-dioneYield 104.7%

Reagents, catalysts & solvents 2

HCID 6212
Chloroform
Solvent
HCID 6344DichloromethaneSolvent

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

  1. customat 0° C
  2. washwashed with water (500 ml×3)
  3. dry with materialAfter drying over magnesium sulfate
  4. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes