Methanol → HCID 21427642, compound

HRID 437989Notes

Reaction equation

HRID 437989 reaction equation
[C:1]([CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1/[CH:17]=[CH:18]/[CH:19]([OH:25])[CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])([O:3]C)=[O:2].CO.C(=O)([O-])[O-].[K+].[K+]>O>[C:1]([CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1/[CH:17]=[CH:18]/[CH:19]([OH:25])[CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])([OH:3])=[O:2]

Participants

5

Reactant 3

HCID 887MethanolHCID 11430Potassium CarbonateHCID 21427639HCID 21427639, compound

Product 1

HCID 21427642HCID 21427642, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 1.28 g. of 1-(6-carbomethoxyhexyl)- 2-(3-hydroxy-trans-1-octenyl)benzene in 150 ml. of methanol is cooled to 0° C. and a solution of 3.0 g. of potassium carbonate in 100 ml. of water is added. The ice bath is removed and the mixture is stirred for twenty-four hours. The methanol is removed in vacuo and the basic aqueous solution is washed with ether, cooled in ice and acidified to pH2 with dilute hydrochloric acid. The solution is then extracted with ether and the extract is washed with water and dried. The solvent is removed to yield 1-(6-carboxyhexyl)-2-(3-hydroxy-trans-1-octenyl)benzene.

Workup

  1. customThe ice bath is removed
  2. customThe methanol is removed in vacuo
  3. washthe basic aqueous solution is washed with ether
  4. temperaturecooled in ice
  5. extractionThe solution is then extracted with ether
  6. washthe extract is washed with water
  7. customdried
  8. customThe solvent is removed

Sources & evidence

ORD record
ord-0d5cb3bedda147839ff39544584c1433
Source dataset
uspto-grants-1977_06
Patent number
US04032656

Reaction notes

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