Water → Methyl 2-(4-(4-hydroxyphenyl)cyclohexylidene)acetate

HRID 632929Notes

Reaction equation

HRID 632929 reaction equation
[H-].[Na+].[CH3:3][O:4][C:5]([CH2:7]P(OC)(OC)=O)=[O:6].[OH:14][C:15]1[CH:20]=[CH:19][C:18]([CH:21]2[CH2:26][CH2:25][C:24](=O)[CH2:23][CH2:22]2)=[CH:17][CH:16]=1.O>O1CCCC1>[CH3:3][O:4][C:5](=[O:6])[CH:7]=[C:24]1[CH2:23][CH2:22][CH:21]([C:18]2[CH:19]=[CH:20][C:15]([OH:14])=[CH:16][CH:17]=2)[CH2:26][CH2:25]1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 80029Trimethyl phosphonoacetateHCID 45989164-(4'-Hydroxyphenyl)cyclohexanone

Product 1

HCID 58909529Methyl 2-(4-(4-hydroxyphenyl)cyclohexylidene)acetateYield 97.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

60% suspension mixed with NaH mineral oil (7.6 g, 0.19 mol) was added to trimethyl phosphonoacetate (22.8 mL, 0.15 mol) solution dissolved in anhydrous tetrahydrofuran (655 mL) under 0° C. nitrogen gas. 4-(4-hydroxyphenyl)cyclohexanone (25 g, 0.13 mol) solution dissolved in tetrahydrofuran (525 mL) was slowly added thereto at 25° C. Then, the reaction mixture was stirred at room temperature for 5 hours, cooled with water, and extracted with ethyl acetate. The mixed organic phase was washed with brine and dried with Na2SO4. The solvent was reduced under reduced pressure to obtain [4-(4-hydroxyphenyl)cyclohexylidene]acetic acid methyl ester as a white solid (31.3 g, 97%).

Workup

  1. additionwas slowly added
  2. customat 25° C
  3. extractionextracted with ethyl acetate
  4. washThe mixed organic phase was washed with brine
  5. dry with materialdried with Na2SO4

Sources & evidence

ORD record
ord-8de431a431d64cc989bebc2a9d21e5e0
Source dataset
uspto-grants-2016_04
Patent number
US09321728B2

Reaction notes

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