Hydrochloric Acid → HCID 54110740, compound

HRID 1732262Notes

Reaction equation

HRID 1732262 reaction equation
C([O:3][C:4](=O)[CH:5]=[C:6]([CH3:21])[CH2:7][CH2:8][CH2:9][CH:10]([CH3:20])[CH2:11][O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)C.[H-].[Al+3].[Li+].[H-].[H-].[H-].Cl>CCOCC>[CH2:13]([O:12][CH2:11][CH:10]([CH3:20])[CH2:9][CH2:8][CH2:7][C:6]([CH3:21])=[CH:5][CH2:4][OH:3])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 21226445Aluminium lithium hydrideHCID 54548634HCID 54548634, compound

Product 1

HCID 54110740HCID 54110740, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent3×

Conditions

Temperature
0 °C

Procedure

Ethyl-8-benzyloxy-3,7-dimethyl-2-octenoate (94.6 g, 0.31 M) in ether (1.4 l) is added to a slurry of lithium aluminum hydride (47.3 g, 1.25 M) in ether (3.3 l) at 0° C. and the reaction mixture is allowed to stir at 0° C. for 4 hours. Wet ether (750 ml) is added slowly and the mixture is acidified with 1N hydrochloric acid. The organic phase is separated, the aqueous phase is extracted with ether and the combined organic extracts are washed with brine and dried (Na2SO4). The solvent is removed in vacuo to give the crude product (77.6 g, 95%). Purification over silica gel using an ethyl acetate/hexane gradient as the eluent gives fractions of varying mixtures of isomers. A collection of fractions that gives 17.7 g of 8-benzyloxy-3,7-dimethyl-2-octenolwith an 85/15 E/Z isomer ratio by gas chromatography analysis is used in the next step:

Workup

  1. customThe organic phase is separated
  2. extractionthe aqueous phase is extracted with ether
  3. washthe combined organic extracts are washed with brine
  4. dry with materialdried (Na2SO4)
  5. customThe solvent is removed in vacuo
  6. customto give the crude product (77.6 g, 95%)
  7. customPurification over silica gel using an ethyl acetate/hexane gradient as the eluent
  8. customgives fractions of varying mixtures of isomers
  9. customA collection of fractions that
  10. customgives 17.7 g of 8-benzyloxy-3,7-dimethyl-2-octenolwith an 85/15 E/Z isomer ratio by gas chromatography analysis

Sources & evidence

ORD record
ord-0bd77cfacbde4401af1cc00fe144dd81
Source dataset
uspto-grants-1980_12
Patent number
US04237055

Reaction notes

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