Hydrochloric Acid → HCID 12010648, compound

HRID 2305276Notes

Reaction equation

HRID 2305276 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][O:7][C:8]12[CH2:24][CH:12]3[CH2:13][C:14]([O:17][CH2:18][O:19][CH2:20][CH2:21][O:22][CH3:23])([CH2:16][C:10](C(OCCCC)=O)([CH2:11]3)[CH2:9]1)[CH2:15]2.[CH3:32][Mg]Br.Cl.[OH-].[Na+].[CH2:38]1[CH2:42][O:41]CC1>>[CH3:32][C:42]([CH3:38])([C:10]12[CH2:16][C:14]3([O:17][CH2:18][O:19][CH2:20][CH2:21][O:22][CH3:23])[CH2:13][CH:12]([CH2:24][C:8]([O:7][CH2:6][O:5][CH2:4][CH2:3][O:2][CH3:1])([CH2:15]3)[CH2:9]1)[CH2:11]2)[OH:41]

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 23435154HCID 23435154, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 12010648HCID 12010648, compound

Procedure

A solution of 100 mmole of the above-prepared n-butyl 3,5-bis(2-methoxyethoxymethoxy)-1-adamantanecarboxylate in 150 ml of THF was added dropwise to the above-prepared methylmagnesium bromide solution in such a rate that the solvent 4 was gently refluxed. The reflux operation was continued for further 2 hours after the completion of addition. The resulting reaction mixture was added dropwise to a 10% by weight hydrochloric acid cooled on ice, while stirring, and the mixture was stirred for further 2 hours at a temperature in a range from 0° C. to room temperature. A 10% by weight aqueous sodium hydroxide solution was added to the reaction mixture to adjust the mixture to around neutrality, and the neutralized mixture was separated to an organic layer and an aqueous layer; the aqueous layer was extracted with toluene; the organic layer was concentrated; and the concentrate was subjected to column chromatography on a silica gel to yield α,α-dimethyl-3,5-bis(2-methoxyethoxymethoxy)-1-adamantanemethanol.

Workup

  1. temperaturewas gently refluxed
  2. additionafter the completion of addition
  3. customThe resulting reaction mixture
  4. temperaturecooled on ice
  5. stirringthe mixture was stirred for further 2 hours at a temperature in a range from 0° C. to room temperature
  6. customthe neutralized mixture was separated to an organic layer
  7. extractionthe aqueous layer was extracted with toluene
  8. concentrationthe organic layer was concentrated

Sources & evidence

ORD record
ord-9e387d3fefd3465d9ef8c20aa60784b9
Source dataset
uspto-grants-2002_08
Patent number
US06440636B1

Reaction notes

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