Hydrochloric Acid → 1-(3-Chloro-4-cyclohexylphenyl)ethane-1,2-diol

HRID 839655Notes

Reaction equation

HRID 839655 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl:7][C:8]1[CH:9]=[C:10]([C:20](=[O:26])[C:21](OCC)=[O:22])[CH:11]=[CH:12][C:13]=1[CH:14]1[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1.Cl>CCOCC>[Cl:7][C:8]1[CH:9]=[C:10]([CH:20]([OH:26])[CH2:21][OH:22])[CH:11]=[CH:12][C:13]=1[CH:14]1[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 12939850Ethyl 3-chloro-4-cyclohexylphenylglyoxylateHCID 21226445Aluminium lithium hydride

Product 1

HCID 129398511-(3-Chloro-4-cyclohexylphenyl)ethane-1,2-diol

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To lithium aluminum hydride solution (3.9 M; 120 ml) diluted with anhydrous ether (750 ml) is added dropwise 150 g of ethyl 3-chloro-4-cyclohexylphenylglyoxylate with stirring, under nitrogen. The mixture is diluted with 250 ml. of ether, and is stirred for 2 hours. The reaction mixture is acidified with 10% hydrochloric acid (450 ml) and extracted with ether/tetrahydrofuran. The aqueous fraction is washed three times with 50 ml portions of ether. The combined ether fractions are washed with water until neutral to litmus, and is dried over potassium carbonate. The ether is removed and the residue is triturated with n-hexane, filtered and air-dried to give 1-(3-chloro-4-cyclohexylphenyl)-1,2-ethanediol.

Workup

  1. additionThe mixture is diluted with 250 ml
  2. extractionextracted with ether/tetrahydrofuran
  3. washThe aqueous fraction is washed three times with 50 ml portions of ether
  4. washThe combined ether fractions are washed with water until neutral to litmus, and
  5. dry with materialis dried over potassium carbonate
  6. customThe ether is removed
  7. customthe residue is triturated with n-hexane
  8. filtrationfiltered
  9. customair-dried

Sources & evidence

ORD record
ord-7d30450bdf6545f588d9d332ec40bc9e
Source dataset
uspto-grants-1978_06
Patent number
US04096279

Reaction notes

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