Sulfuric Acid → HCID 4550710, compound

HRID 1155794Notes

Reaction equation

HRID 1155794 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][C:8]12[CH2:22][C:12]3([C:23](OCC)=[O:24])[CH2:13][C:14]([C:17](OCC)=[O:18])([CH2:16][C:10]([CH3:28])([CH2:11]3)[CH2:9]1)[CH2:15]2.CCOC(C)=O.OS(O)(=O)=O>CCOCC>[CH3:28][C:10]12[CH2:16][C:14]3([CH2:17][OH:18])[CH2:13][C:12]([CH2:23][OH:24])([CH2:22][C:8]([CH3:7])([CH2:15]3)[CH2:9]1)[CH2:11]2

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 8857Ethyl AcetateHCID 616593HCID 616593, compoundHCID 21226445Aluminium lithium hydride2×

Product 1

HCID 4550710HCID 4550710, compoundYield 87.4%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

Six grams of lithium-aluminum hydride (0.158 mole) was stirred with 200 ml of absolute ether and to this was added dropwise 24.15 g (0.078 mole) of diethyl 1,3-dimethyladamantane-5,7-dicarboxylate in 50 ml of absolute ether at a rate such as to maintain gentle refluxing of the solvent. Refluxing was continued for two hours. Then the excess LiAlH4 was decomposed with moist AcOEt. The reaction mixture was acidified with 20% H2SO4 which gave, by crystallization, 15.3 g of 1,3-dimethyl-5,7-bis (hydroxymethyl)-adamantane (IIb) which was collected by filtration. Another 1.8 g crop was obtained from the filtrate after separating the water phase and evaporating the organic layer. Yield was 17.1 g (97%). MP was 158°-161° C. Recrystallization from ethyl acetate afforded a product MP 160°-162° C.

Workup

  1. temperatureto maintain gentle
  2. temperaturerefluxing of the solvent
  3. temperatureRefluxing

Sources & evidence

ORD record
ord-7a1a95d3ae614ec6a2f465b6ef9f57e2
Source dataset
uspto-grants-1982_06
Patent number
US04332964

Reaction notes

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