Diethoxymethane → HCID 123658901, compound

HRID 716482Notes

Reaction equation

HRID 716482 reaction equation
[CH:1]1([OH:13])[CH2:12][CH2:11][CH2:10][CH:9]=[CH:8][CH2:7][CH2:6][CH:5]=[CH:4][CH2:3][CH2:2]1.[CH2:14]([O:16][CH2:17]OCC)[CH3:15].[Br-].[Li+].O.C1(C)C(S(O)(=O)=O)=CC=CC=1>CC(OC)(C)C>[CH2:14]([O:16][CH2:17][O:13][CH:1]1[CH2:12][CH2:11][CH2:10][CH:9]=[CH:8][CH2:7][CH2:6][CH:5]=[CH:4][CH2:3][CH2:2]1)[CH3:15]

Participants

6

Reactant 4

HCID 10024DiethoxymethaneHCID 82050Lithium BromideHCID 124969952-Methylbenzenesulfonic acid hydrateHCID 57065501Cyclododeca-4,8-dien-1-ol

Product 1

HCID 123658901HCID 123658901, compound

Reagents, catalysts & solvents 1

HCID 15413tert-Butyl methyl etherSolvent

Procedure

To a mechanically stirred mixture of 4,8-cyclododecadien-1-ol (5.4 g, 30 mmol; in the form of a 47% E,Z-, 48% Z,E- and 5% E,E isomer mixture), formaldehyde diethyl acetal (31.2 g, 294 mmol) and lithium bromide (0.52 g, 6 mmol) was added toluene sulphonic acid monohydrate (0.57 g, 3 mmol). The mixture was stirred at room temperature for 3 hours, then diluted with MTBE, washed with aqueous NaHCO3, water and brine. The solvent was evaporated and the product purified by liquid chromatography (silica gel 230 g; eluent=heptane/ethyl acetate 95/5).

Workup

  1. washwashed with aqueous NaHCO3, water and brine
  2. customThe solvent was evaporated
  3. customthe product purified by liquid chromatography (silica gel 230 g; eluent=heptane/ethyl acetate 95/5)

Sources & evidence

ORD record
ord-a4da2359c18f4d32b14d5764b5b10059
Source dataset
uspto-grants-2015_11
Patent number
US09187710B2

Reaction notes

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