Sodium Hydroxide → HCID 66584185, compound

HRID 716488Notes

Reaction equation

HRID 716488 reaction equation
C([O:4][CH2:5]/[CH:6]=[C:7](\[CH3:15])/[CH2:8][C:9]1[CH2:14][CH2:13][CH2:12][CH2:11][CH:10]=1)(=O)C.[OH-].[Na+]>O>[C:9]1([CH2:8]/[C:7](/[CH3:15])=[CH:6]/[CH2:5][OH:4])[CH2:14][CH2:13][CH2:12][CH2:11][CH:10]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 66584078HCID 66584078, compound

Product 1

HCID 66584185HCID 66584185, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
92.5 °C

Procedure

(2E)-4-cyclohexenyl-3-methylbut-2-enyl acetate (2.08 kg, 10.0 mols, purity: 98%) sodium hydroxide (420 g, 10.5 mols) and water (8400 ml) were mixed together and heated at 90-95° C. under stirring for 10-12 h. The reaction mixture was cooled to 35° C. The aqueous phase was separated from the organic phase. The organic phase was washed once with 5% w/w aqueous NaCl and twice with water. The crude product was fractionated under reduced pressure to provide (2E)-4-cyclohexenyl-3-methylbut-2-en-1-ol (1.5 kg, yield: 93%; GC purity: 99% sum of the isomers). Reduced pressure (1 mmHg) to give 1.54 kg of (2E)-4-(cyclohex-1-en-1-yl)-3-methylbut-3-en-1-ol and (2E) isomer (yield: 93%; GC purity: 99% sum of the isomers).

Workup

  1. temperatureThe reaction mixture was cooled to 35° C
  2. customThe aqueous phase was separated from the organic phase
  3. washThe organic phase was washed once with 5% w/w aqueous NaCl and twice with water

Sources & evidence

ORD record
ord-c9708862fa8a4014af1a3e51e13e39db
Source dataset
uspto-grants-2015_11
Patent number
US09187709B2

Reaction notes

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