Water → (S)-2-(3,3-Diphenyl-2-propenyl)-2-ethylcyclohexanone

HRID 247651Notes

Reaction equation

HRID 247651 reaction equation
[CH2:1]([C@@:3]1([CH2:13][CH2:14][C:15]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)O)[CH2:12][CH2:11][CH2:10][CH2:9][C:4]21OCC[O:5]2)[CH3:2].O>C(O)(=O)C>[C:17]1([C:15]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[CH:14][CH2:13][C@:3]2([CH2:1][CH3:2])[CH2:12][CH2:11][CH2:10][CH2:9][C:4]2=[O:5])[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

4

Reactant 2

HCID 962WaterHCID 54110677(S)-6-Ethyl-alpha,alpha-diphenyl-1,4-dioxaspiro[4.5]decane-6-propanol

Product 1

HCID 53977647(S)-2-(3,3-Diphenyl-2-propenyl)-2-ethylcyclohexanone

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of (S)-6-ethyl-α,α-diphenyl-1,4-dioxaspiro[4.5]decane-6-propanol (175 g) in 1 L of acetic acid containing 50 mL of water was refluxed for 3.5 hours. Most of the acetic acid was removed on a rotary evaporator, and the oily residue was poured into 300 mL of water. It was extracted with ether (2×300 mL) and the extracts were combined. They were washed with 1M sodium hydroxide (2×150 mL, first wash neutral, second wash basic) and brine (300 mL). Concentration afforded 140 g of cloudy brown oil.

Workup

  1. customMost of the acetic acid was removed on a rotary evaporator
  2. additionthe oily residue was poured into 300 mL of water
  3. extractionIt was extracted with ether (2×300 mL)
  4. washThey were washed with 1M sodium hydroxide (2×150 mL, first wash neutral, second wash basic) and brine (300 mL)
  5. concentrationConcentration
  6. customafforded 140 g of cloudy brown oil

Sources & evidence

ORD record
ord-e509602c5afd411eb507c0e0eeec5e59
Source dataset
uspto-grants-1987_11
Patent number
US04709048

Reaction notes

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